Oxime-substituted amide compound and pest control agent

ABSTRACT

To provide a novel pesticide, especially a fungicide and a nematocide. 
     An oxime-substituted amide compound represented by the formula (I) or its salt, and a pesticide containing it: 
     
       
         
         
             
             
         
       
     
     wherein G 1  is a structure represented by G 1 -1 or the like, G 2  is a structure represented by G 2 -2 or the like: 
     
       
         
         
             
             
         
       
     
     W is an oxygen atom or the like, X 1  is a halogen atom, methyl, trifluoromethyl or the like, each of X 2 , X 3 , X 4  and X 5  is independently a hydrogen atom, a halogen atom or the like, each of Y 1  and Y 3  is independently a halogen atom, cyano, methyl, trifluoromethyl, C 2 -C 6  alkynyl or the like, each of Y 2  and Y 4  is independently a hydrogen atom, a halogen atom or the like, R 1  is C 1 -C 6  alkyl, C 1 -C 4  haloalkyl, (C 1 -C 4 )alkyl substituted with R 18 , C 3 -C 6  cycloalkyl, C 3 -C 6  alkenyl or the like, each of R 2  and R 3  is independently a hydrogen atom, methyl or the like, R 4  is a hydrogen atom or the like, R 18  is C 3 -C 6  cycloalkyl, phenyl, phenyl substituted with (Z) m  or the like, Z is a halogen atom or the like, and m is an integer of 1, 2 or 3.

TECHNICAL FIELD

The present invention relates to a novel oxime-substituted amidecompound or its salt, and a pesticidal composition containing thecompound as an active ingredient.

BACKGROUND ART

Heretofore, with respect to oxime-substituted amide compounds,N-[2-(methoxyimino)-2-phenylethyl]-4-(trifluoromethyl)nicotinamide and3-iodo-N²-[2-(methoxyimino)-2-phenylethyl]-N¹-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]phthalicacid diamide are known to have insecticidal activity (for example,Patent Documents 1 and 2).

Further, 2-chloro-N-[2-(4-chlorophenyl)-2-(methoxyimino)ethyl]benzamide,N-[2-(4-chlorophenyl)-2-(methoxyimino)ethyl]-2,4-dichlorobenzamide andthe like are known to alter the lifespan of eukaryotic organisms (PatentDocument 3).

Further, certain pyrazole-4-carboxamide derivatives are known to havefungicidal activity (for example, Patent Documents 4 to 7).

However, the oxime-substituted amide compound of the present inventionis not disclosed at all, and its usefulness as a pesticide has not beenknown.

PRIOR ART DOCUMENTS Patent Documents

-   Patent Document 1: JP-A-2004-035439-   Patent Document 2: WO2001/021576-   Patent Document 3: U.S. Patent Application Publication No.    2009/0163545-   Patent Document 4: WO2001-055136-   Patent Document 5: WO2009-127722-   Patent Document 6: WO2011-151369-   Patent Document 7: WO2011-151370

DISCLOSURE OF INVENTION Technical Problem

Infection or parasitism of pests such as pathogens and parasites causes,in a case where the hosts are plants such as grain, fruits, vegetablesor ornamental plants, a decrease in the quality of agricultural cropsand a remarkable decrease in the yield, and in some cases, seriousdamages such as death of the plants, and inflicts heavy economic lossesnot only on the producers but also on the consumers. Thus, toeffectively control such pests is a very important object to achieveefficient and stable production of agricultural crops. Further, in acase where the hosts are animals such as companion creatures/pets orlivestock/poultry, to effectively control such pests is an importantobject also for the purpose of maintaining health of the target animalsand further, in a case where the target animals are livestock orpoultry, for the purpose of stably producing safe food or high qualitygeneral merchandise such as wool, feathers or leathers. From such aviewpoint, heretofore, development of pesticides targeted at pathogensor parasites has advanced, and various effective pesticides have beenput into practical use.

However, recently, control of pests with conventional pesticides hasbecome difficult in more and more cases, as pathogens or parasitesacquire resistance to them over many years of their use. Problems of thehigh toxicity of some conventional pesticides and of the disturbance ofthe ecosystem by some conventional pesticides which remain in theenvironment for a long period are becoming apparent. Under thesecircumstances, development of novel pesticides not only having excellentpesticidal activity on pathogens and parasites but also having highpesticidal properties such as low toxicity and low persistence and of aneffective controlling method is always expected.

Solution to Problem

The present inventors have conducted extensive studies to achieve theabove object and as a result, found that a novel oxime-substituted amidecompound represented by the following formula (I) is a very usefulcompound which is excellent in pesticidal activities, especially inantifungal and nematicidal activities, and has little harmful effect onnon-target organisms such as plants, mammals, fishes, useful insects andnatural enemies, and accomplished the present invention.

That is, the present invention relates to an oxime-substituted amidecompound represented by the formula (I), or its N-oxide or salt:

wherein G¹ is a structure represented by any one of G¹-1 to G¹-51:

G² is a structure represented by any one of G²-1 to G²-19:

W is an oxygen atom or a sulfur atom,

X¹ is a halogen atom, cyano, nitro, —SF₅, C₁-C₆ alkyl, (C₁-C₆)alkyloptionally substituted with R⁶, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,—OR⁷, —S(O)_(r)R⁷, —N(R⁹)R⁸, —C(O)NH₂, —C(S)NH₂, tri(C₁-C₈ alkyl)silyl,phenyl, phenyl substituted with (Z)_(m) or D-3,

each of X², X³, X⁴ and X⁵ is independently a hydrogen atom, a halogenatom, cyano, nitro, C₁-C₈ alkyl, (C₁-C₆)alkyl optionally substitutedwith R⁶, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, —OH, —OR⁷, —SH,—S(O)_(r)R⁷, —N(R⁹)R⁸, C₁-C₆ alkylcarbonyl, C₁-C₈ alkoxycarbonyl,—C(O)NH₂, —C(S)NH₂, phenyl, phenyl substituted with (Z)_(m), D-2 orD-32,

provided that when G₁ is a structure represented by G¹-27 and X¹ isdihalomethyl, X² is a hydrogen atom,

each of Y¹ and Y³ is independently a hydrogen atom, a halogen atom,cyano, nitro, —SCN, —SF₅, C₁-C₈ alkyl, (C₁-C₆)alkyl optionallysubstituted with R⁶, C₃-C₁₀ cycloalkyl, (C₃-C₁₀)cycloalkyl optionallysubstituted with R⁶, E-1 to E-22, C₂-C₆ alkenyl, (C₂-C₆)alkenyloptionally substituted with R⁶, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, C₂-C₆ alkynyl, (C₂-C₆)alkynyl optionally substitutedwith R⁶, —OH, —OR⁷, —OS(O)₂R⁷, —SH, —S(O)_(r)R⁷, —N(R⁹)R⁸,—N═C(R^(9a))R^(8a), —C(O)R¹⁰, —C(R¹⁰)═NOH, —C(R¹⁶)═NOR¹¹, M-3, M-13,M-30, —C(O)OH, —C(O)OR¹¹, —C(O)SR¹¹, —C(O)N(R¹³)R¹², M-7, M-17, M-23,M-26, —C(S)OR¹¹, —C(S)SR¹¹, —C(S)N(R¹³)R¹², M-9, M-19, M-23, M-24, M-28,M-25, M-29, —S(O)₂OR¹¹, —S(O)₂N(R¹³)R¹², —Si(R^(14a))(R^(14b))R¹⁴,phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38,

each of Y², Y⁴ and Y⁶ is independently a hydrogen atom, a halogen atom,cyano, nitro, —SCN, —SF₅, C₁-C₆ alkyl, (C₁-C₆)alkyl optionallysubstituted with R⁶, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, —OH, —OR⁷,—SH, —S(O)_(r)R⁷, —NH₂, C₁-C₆ alkylamino, di(C₁-C₆ alkyl)amino, C₂-C₆alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₁-C₆alkoxycarbonyl, —C(O)NH₂ or —C(S)NH₂,

or, Y¹, Y², Y³ and Y⁴ represent that Y¹ or Y³ and Y², or Y³ and Y⁴,together form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—,—CH₂CH₂CH₂CH₂—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂N(R⁵)—,—CH₂N(R)CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—,—OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —CH₂CH═CH—, —N(R⁵)N═CH—,—OCH₂CH═CH—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═N— or—N═CHCH═N— to form a 5-membered ring or a 6-membered ring together withthe carbon atoms attached to Y¹, Y², Y³ and Y⁴, wherein hydrogen atomson the respective ring-constituting carbon atoms may optionally besubstituted with a halogen atom, cyano, nitro, C₁-C₄ alkyl or C₁-C₄haloalkyl,

and further, when G¹ is a structure represented by G¹-1, G¹-9, G¹-10,G¹-12, G¹-13, G¹-16 to G¹-20, G¹-22 to G¹-24, G¹-26, G¹-27, G¹-30,G¹-32, G¹-35, G¹-38, G¹-40 or G¹-42 to G¹-50, Y¹ and Y², Y² and Y³, orY³ and Y⁴, together may form —OCH═CH—, —SCH═CH—, —N(R⁵)CH═CH—, —OCH═N—,—SCH═N— or —N(R⁵)CH═N— to form a 5-membered ring together with thecarbon atoms attached to Y¹, Y², Y³ and Y⁴, wherein hydrogen atoms onthe respective ring-constituting carbon atoms may optionally besubstituted with a halogen atom, cyano, nitro, C₁-C₄ alkyl or C₁-C₄haloalkyl,

D-1 to D-38 are aromatic heterocyclic rings represented by the followingstructural formulae, respectively:

E-1 to E-22 are saturated heterocyclic rings represented by thefollowing structural formulae, respectively:

Z is a halogen atom, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, C₁-C₄ haloalkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, C₁-C₄ haloalkylthio(C₁-C₄)alkyl, C₁-C₄alkylsulfinyl(C₁-C₄)alkyl, C₁-C₄ haloalkylsulfinyl(C₁-C₄)alkyl, C₁-C₄alkylsulfonyl(C₁-C₄)alkyl, C₁-C₄ haloalkylsulfonyl(C₁-C₄)alkyl, C₃-C₆cycloalkyl, C₃-C₆ halocycloalkyl, —OH, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylsulfonyloxy, C₁-C₄ haloalkylsulfonyloxy, C₁-C₄ alkylthio,C₁-C₄ haloalkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylsulfonyl, —NH₂, C₁-C₄ alkylamino, di(C₁-C₄alkyl)amino, C₁-C₄ alkoxycarbonyl, C₁-C₄ haloalkoxycarbonyl, —C(O)NH₂,C₁-C₄ alkylaminocarbonyl, di(C₁-C₄ alkyl)aminocarbonyl, —C(S)NH₂,—S(O)₂NH₂ or phenyl,

when m or n is an integer of at least 2, the respective is may beidentical with or different from one another, and when there are twoneighboring Z's, the two neighboring Z's may form —CH₂CH₂CH₂—,—CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—,—CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—,—OCH₂CH₂S— or —CH═CH—CH═CH— to form a 5-membered ring or a 6-memberedring together with the carbon atoms attached to the two is, whereinhydrogen atoms on the respective ring-constituting carbon atoms mayoptionally be substituted with a halogen atom, a cyano group, a nitrogroup, a methyl group, a trifluoromethyl group, a methoxy group or amethylthio group,

R¹ is C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substituted with R¹⁸, C₃-C₁₀cycloalkyl, C₃-C₁₀ halocycloalkyl, E-2 to E-8, E-14 to E-18, E-21, C₃-C₆alkenyl, C₃-C₆ haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl,phenyl(C₃-C₆)alkynyl, phenyl or phenyl substituted with (Z)_(m),

R² is a hydrogen atom, cyano, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄alkylsulfinyl(C₁-C₄)alkyl, C₁-C₄ alkylsulfonyl(C₁-C₄)alkyl, C₃-C₆cycloalkyl or phenyl, or may form the after-mentioned ring together withR³,

provided that when G¹ is a structure represented by G¹-1, X¹ is achlorine atom, X², X³ and X⁵ are hydrogen atoms, X⁴ is a hydrogen atomor a chlorine atom, G² is a structure represented by G²-1, Y³ is achlorine atom, and Y¹, Y², Y⁴ and Y⁵ are hydrogen atoms, R² is cyano,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, C₁-C₄ alkylsulfinyl(C₁-C₄)alkyl, C₁-C₄alkylsulfonyl(C₁-C₄)alkyl, C₃-C₆ cycloalkyl or phenyl,

R³ is a hydrogen atom or C₁-C₆ alkyl,

or R³ may form, together with R², a C₂-C₅ alkylene chain to form a 3- to6-membered ring together with the carbon atom attached to R² and R³,wherein the alkylene chain may contain an oxygen atom, sulfur atom ornitrogen atom, and may optionally be substituted with a C₁-C₄ alkylgroup, a —CHO group, a C₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonylgroup, a C₁-C₄ alkylaminocarbonyl group, a C₁-C₄ haloalkylaminocarbonylgroup, a di(C₁-C₄ alkyl)aminocarbonyl group or a phenyl group,

R⁴ is a hydrogen atom, cyano, nitro, C₁-C₆ alkyl, (C₁-C₆)alkyloptionally substituted with R¹⁹, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₃-C₆alkynyl, C₃-C₆ haloalkynyl, —C(O)R²⁰, —C(O)OR²¹, —C(O)SR²¹,—C(O)N(R²³)R²², —C(O)C(O)OR²¹, —C(S)OR²¹, —C(S)SR²¹, —C(S)N(R²³)R²²,—OH, —OR²¹, —SR²¹, —N(R²⁵)R²⁴, —N═C(R^(25a))R^(24a), —S(O)₂R²¹,—S(O)₂N(R²³)R²² or —SN(R²⁷)R²⁶,

R⁵ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl(C₁-C₄)alkyl, C₃-C₆ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl,

R⁶ is a halogen atom, cyano, nitro, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, hydroxy(C₃-C₈)cycloalkyl, C₁-C₆ alkoxy(C₃-C₈)cycloalkyl,C₃-C₆ alkenyl, C₃-C₈ cycloalkenyl, E-1 to E-22, —OH, —OR⁷, —SH,—S(O)_(r)R⁷, —N(R⁹)R⁸, —C(R¹⁰)═NOH, —C(R¹⁰)═NOR¹¹, —C(O)OR¹¹,—C(O)N(R¹³)R¹², —Si(R^(14a))(R^(14b))R¹⁴, phenyl, phenyl substitutedwith (Z)_(m) or D-1 to D-38,

R⁷ is C₁-C₆ alkyl, (C₁-C₆) alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted with R²⁸, E-2 toE-8, E-14 to E-18, E-21, C₂-C₆ alkenyl, (C₂-C₆)alkenyl optionallysubstituted with R²⁸, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl,C₃-C₆ alkynyl, (C₃-C₆)alkynyl optionally substituted with R²⁸, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxycarbonyl, phenyl, phenyl substituted with(Z)_(m), D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23,D-25, D-27 or D-30 to D-38,

R⁸ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, —C(O)R¹⁰, —C(O)C(O)R¹¹,—C(O)OR¹¹, —C(O)C(O)OR¹¹, —C(O)SR¹¹, —C(O)N(R¹³)R¹², —C(S)OR¹¹,—C(S)SR¹¹, —C(S)N(R¹³)R¹², —OH, —S(O)₂R¹¹ or —S(O)₂N(R¹³)R¹², or mayform the after-mentioned ring together with R⁹,

R⁹ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆alkynyl, C₃-C₆ haloalkynyl, —CHO, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl or C₁-C₆ alkoxycarbonyl,

or R⁹ may form, together with R⁸, a C₂-C₆ alkylene chain to form a 3- to7-membered ring together with the nitrogen atom attached to R⁸ and R⁹,wherein the alkylene chain may contain an oxygen atom, sulfur atom ornitrogen atom, and may optionally be substituted with a halogen atom, aC₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, an oxo group or a thioxogroup,

R^(8a) is C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ alkenyloxy,phenoxy or phenoxy substituted with (Z)_(m), or may form theafter-mentioned ring together with R^(9a),

R^(9a) is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,phenyl or phenyl substituted with (Z)_(m),

or R^(9a) may form, together with R^(8a), a C₄-C₆ alkylene chain to forma 5- to 7-membered ring together with the carbon atom attached to R^(8a)and R^(9a), wherein the alkylene chain may contain an oxygen atom orsulfur atom,

R¹⁰ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₂-C₆alkynyl, C₂-C₆ haloalkynyl, phenyl, phenyl substituted with (Z)_(m), orD-1 to D-38,

R¹¹ is C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl,C₆-C₁₀ cycloalkenyl, C₆-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with (Z)_(m), D-1, D-2, D-4 toD-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,

R¹² is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, C₁-C₆ alkylcarbonyl,C₁-C₆ haloalkylcarbonyl, phenylcarbonyl, C₁-C₆ alkoxycarbonyl, phenyl,phenyl substituted with (Z)_(m), D-1 to D-25 or D-27 to D-38, or mayform the after-mentioned ring together with R¹³,

R¹³ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, C₁-C₄ alkylsulfonyl(C₁-C₄)alkyl,cyano(C₁-C₄)alkyl, C₃-C₆ alkenyl or C₃-C₆ alkynyl,

or R¹³ may form, together with R¹², a C₂-C₆ alkylene chain to form a 3-to 7-membered ring together with the nitrogen atom attached to R¹² andR¹³, wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a —CHO group, a C₁-C₄alkylcarbonyl group or a C₁-C₄ alkoxycarbonyl group,

R¹⁴ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, phenyl or phenylsubstituted with (Z)_(m),

each of R^(14a) and R^(14b) is independently C₁-C₆ alkyl, C₁-C₆haloalkyl or C₁-C₆ alkoxy,

R¹⁵ is a hydrogen atom, cyano, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl(C₁-C₄)alkyl, hydroxy(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl,C₁-C₄ haloalkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄haloalkylthio(C₁-C₄)alkyl, C₁-C₄ alkylamino(C₁-C₄)alkyl, di(C₁-C₄alkyl)amino(C₁-C₄)alkyl, cyano(C₁-C₄)alkyl, C₁-C₄alkoxycarbonyl(C₁-C₄)alkyl, C₁-C₄ haloalkoxycarbonyl(C₁-C₄)alkyl,phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₆cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆haloalkynyl, C₁-C₆ alkylcarbonyl, phenylcarbonyl, phenylcarbonylsubstituted with (Z)_(m), C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, di(C₁-C₆ alkyl)aminocarbonyl, C₁-C₆ alkylsulfonyl,phenylsulfonyl, phenylsulfonyl substituted with (Z)_(m), di(C₁-C₆alkyl)aminosulfonyl, phenyl, phenyl substituted with (Z)_(m), or C₁-C₆alkoxy,

and further, when R¹⁵ and Z are neighboring, the neighboring R¹⁵ and Zmay form —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—,—CH═CH—N═CH— or —CH═CH—CH═N— to form a 6-membered ring together with theatoms respectively attached to R¹⁵ and Z, wherein hydrogen atoms on therespective ring-constituting carbon atoms may optionally be substitutedwith a halogen atom, a methyl group or a trifluoromethyl group,

R¹⁶ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl,C₃-C₆ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,C₃-C₆ haloalkynyl, —C(O)R¹⁰, —C(O)C(O)R¹¹, —C(O)OR¹¹, —C(O)C(O)OR¹¹,—C(O)SR¹¹, —C(O)N(R¹³)R¹², —C(S)OR¹¹, —C(S)SR¹¹, —C(S)N(R¹³)R¹²,—S(O)₂R¹¹, —S(O)₂N(R¹³)R¹², phenyl, phenyl substituted with (Z)_(m) orD-3,

R^(16a) is a hydrogen atom, cyano, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ haloalkoxycarbonyl, C₁-C₆ alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R¹⁷ is a halogen atom, cyano, C₁-C₆ alkyl, C₁-C₆ haloalkyl,hydroxy(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄) alkyl, C₁-C₄alkoxycarbonyl(C₁-C₄)alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆alkylamino, di(C₁-C₆ alkyl)amino, C₁-C₆ alkoxycarbonyl, phenyl or phenylsubstituted with (Z)_(m),

when p is an integer of at least 2, the respective R¹⁷'s may beidentical with or different from one another, and further, when twoR¹⁷'s are on the same carbon atom, the two R¹⁷'s together may form C₁-C₄alkylidene, oxo, thioxo, imino, C₁-C₄ alkylimino or C₁-C₄ alkoxyimino,

R¹⁸ is a halogen atom, cyano, nitro, C₃-C₁₀ cycloalkyl, C₃-C₁₀halocycloalkyl, E-1 to E-22, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, —OR²⁹, —N(R³⁰)R²⁹, —SH, —S(O)_(r)R³¹,—S(O)_(t)(R³¹)═NR^(16a), —C(O)R³², —C(R³²)═NOH, —C(R³²)═NOR³³, —C(O)OH,—C(O)OR³³, —C(O)SR³³, —C(O)N(R³⁵)R³⁴, —C(O)C(O)OR³³, —C(S)OR³³,—C(S)SR³³, —C(S)N(R³⁵)R³⁴, —S(O)₂OH, —S(O)₂OR³³, —S(O)₂N(R³⁵)R³⁴,—Si(R^(14a))(R^(14b))R¹⁴, M-1 to M-30, phenyl, phenyl substituted with(Z), or D-1 to D-38,

M-1 to M-30 are partial saturated heterocyclic rings represented by thefollowing structural formulae, respectively:

R¹⁹ is a halogen atom, cyano, nitro, C₃-C₈ cycloalkyl, E-5, E-6, E-14,E-15, C₈-C₁₀ cycloalkenyl, —OR³⁶, —S(O)_(r)R³⁷, —C(R³²)═NOH,—C(R³²)═NOR³³, M-3, —C(O)OR³³, —C(O)SR³³, —C(O)NH₂, M-7, M-17,—C(O)C(O)OR³³, —C(S)OR³³, —C(S)SR³³, —C(S)NH₂, M-9, M-19,—S(O)₂N(R³⁵)R³⁴ or —Si(R^(14a))(R^(14b))R¹⁴,

R²⁰ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₂-C₆ alkynylor C₂-C₆ haloalkynyl,

R²¹ is C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl,C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl or C₃-C₆haloalkynyl,

R²² is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, C₁-C₆ alkylcarbonyl,C₁-C₆ haloalkylcarbonyl, phenylcarbonyl, C₁-C₆ alkoxycarbonyl, phenyl,phenyl substituted with (Z)_(m), D-1 to D-25 or D-27 to D-38, or mayform the after-mentioned ring together with R²³,

R²³ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, C₁-C₄ alkylsulfonyl(C₁-C₄)alkyl,cyano(C₁-C₄)alkyl, C₃-C₆ alkenyl or C₃-C₆ alkynyl,

or R²³ may form, together with R²², a C₂-C₆ alkylene chain to form a 3-to 7-membered ring together with the nitrogen atom attached to R²² andR²³, wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a —CHO group, a C₁-C₄alkylcarbonyl group or a C₁-C₄ alkoxycarbonyl group,

R²⁴ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₃-C₈ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl,C₃-C₆ haloalkynyl, —S(O)₂R³³ or —S(O)₂N(R³⁵)R³⁴, or may form theafter-mentioned ring together with R²⁵,

R²⁵ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl,C₃-C₆ haloalkenyl, C₃-C₆ alkynyl or C₃-C₆ haloalkynyl,

or R²⁵ may form, together with R²⁴, a C₄-C₅ alkylene chain to form a 5-to 6-membered ring together with the nitrogen atom attached to R²⁴ andR²⁵, wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a C₁-C₄ alkoxy group, a—CHO group, a C₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group,an oxo group or a thioxo group,

R^(24a) is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkyl, phenyl or phenyl substituted with (Z)_(m), or may form theafter-mentioned ring together with R^(25a),

R^(25a) is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthioor di(C₁-C₆ alkyl)amino,

or R^(25a) may form, together with R^(24a), a C₃-C₅ alkylene chain toform a 4- to 6-membered ring together with the carbon atom attached toR^(24a) and R^(25a), wherein the alkylene chain may contain an oxygenatom, sulfur atom or nitrogen atom, and may optionally be substitutedwith a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a—CHO group, a C₁-C₄ alkylcarbonyl group or a C₁-C₄ alkoxycarbonyl group,

R²⁶ is C₁-C₁₂ alkyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ alkoxy(C₁-C₁₂)alkyl,cyano(C₁-C₁₂)alkyl, C₁-C₁₂ alkoxycarbonyl(C₁-C₁₂)alkyl,phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₁₂alkenyl, C₃-C₁₂ haloalkenyl, C₃-C₁₂ alkynyl, C₃-C₁₂ haloalkynyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂ alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃,—C(O)ON═C(SCH₃)C(O)N(CH₃)₂, phenyl or phenyl substituted with (Z)_(m),or may form the after-mentioned ring together with R²⁷,

R²⁷ is C₁-C₁₂ alkyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ alkoxy(C₁-C₁₂ alkyl),cyano(C₁-C₁₂)alkyl, C₁-C₁₂ alkoxycarbonyl(C₁-C₁₂)alkyl,phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₁₂alkenyl, C₃-C₁₂ haloalkenyl, C₃-C₁₂ alkynyl, C₃-C₁₂ haloalkynyl, phenylor phenyl substituted with (Z)_(m),

or R²⁷ may form, together with R²⁶, a C₄-C₇ alkylene chain to form a 5-to 8-membered ring together with the nitrogen atom attached to R²⁶ andR²⁷, wherein the alkylene chain may contain an oxygen atom or sulfuratom, and may optionally be substituted with a C₁-C₄ alkyl group or aC₁-C₄ alkoxy group,

R²⁸ is a halogen atom, cyano, nitro, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, di(C₁-C₆alkyl)amino, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, —C(O)NH₂,C₁-C₆ alkylaminocarbonyl, di(C₁-C₆ alkyl)aminocarbonyl, —C(S)NH₂,phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38,

R²⁹ is a hydrogen atom, C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substitutedwith R³⁸, C₃-C₈ cycloalkyl, (C₃-C₈)cycloalkyl optionally substitutedwith R³⁸, E-2 to E-6, E-8, E-14 to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyloptionally substituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₈)alkynyloptionally substituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰, —C(O)OR⁴⁰,—C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹, —C(S)OR⁴⁰,—C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹, —S(O)₂R⁴⁰, —S(O)₂N(R⁴²)R⁴¹,—Si(R^(14a))(R^(14b))R¹⁴, P(O)(OR⁴³)₂, —P(S)(OR⁴³)₂, phenyl, phenylsubstituted with (Z)_(m), D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 toD-19, D-21, D-23, D-25, D-27 or D-30 to D-38, or may form theafter-mentioned ring together with R³⁰,

R³⁰ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₄cycloalkyl(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, cyano(C₁-C₄)alkyl, C₃-C₆ cycloalkyl, C₃-C₆alkenyl, C₃-C₆ alkynyl, C₁-C₆ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkoxy, C₁-C₆ alkylsulfonyl, phenyl or phenyl substituted with(Z)_(m),

or R³⁰ may form, together with R²⁹, a C₂-C₈ alkylene chain to form a 3-to 7-membered ring together with the nitrogen atom attached to R²⁹ andR³⁰, wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a C₁-C₄ alkoxy group, a—CHO group, a C₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group, aphenyl group, a phenyl group substituted with (Z)_(m), an oxo group or athioxo group,

R³¹ is C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substituted with R³⁸, C₃-C₈cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 toE-6, E-8, E-14 to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyl optionallysubstituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₈)alkynyl optionallysubstituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰, —C(O)OR⁴⁰, —C(O)C(O)OR⁴⁰,—C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹, —C(S)OR⁴⁰, —C(S)SR⁴⁰,—C(S)N(R⁴²)R⁴¹, —SH, C₁-C₆ alkylthio, C₁-C₈ haloalkylthio, phenylthio,phenylthio substituted with (Z)_(m), —P(O)(OR⁴³)₂, —P(S)(OR⁴³)₂, phenyl,phenyl substituted with (Z)_(m), D-9, D-10, D-12, D-14 to D-17, D-30 orD-32 to D-35,

R³² is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈cycloalkyl(C₁-C₄)alkyl, C₁-C₈ alkoxy(C₁-C₄)alkyl, C₁-C₈haloalkoxy(C₁-C₄)alkyl, C₁-C₈ alkylthio(C₁-C₄)alkyl, C₁-C₆haloalkylthio(C₁-C₄)alkyl, C₁-C₈ alkylsulfonyl(C₁-C₄)alkyl, C₁-C₈haloalkylsulfonyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkylsubstituted with (Z)_(m), C₃-C₈ cycloalkyl, phenyl or phenyl substitutedwith (Z)_(m),

R³³ is C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substituted with R³⁸, C₃-C₈cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 toE-6, E-8, E-14 to E-21, C₂-C₈ alkenyl, (C₂-C₆)alkenyl optionallysubstituted with R³⁸, C₃-C₆ alkynyl, (C₃-C₆)alkynyl optionallysubstituted with R³⁸, phenyl, phenyl substituted with (Z)_(m), D-1, D-2,D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 toD-38,

R³⁴ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R³⁸, C₃-C₈ cycloalkyl, (C₃-C₈)cycloalkyl optionally substitutedwith R³⁸, E-2 to E-6, E-8, E-14 to E-21, C₂-C₆ alkenyl, (C₂-C₆)alkenyloptionally substituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₆)alkynyloptionally substituted with R³⁸, phenyl, phenyl substituted with(Z)_(m), D-1 to D25 or D-27 to D-38, or may form the after-mentionedring together with R³⁵,

R³⁵ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R³⁸, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(m),

or R³⁵ may form, together with R³⁴, a C₂-C₅ alkylene chain to form a 3-to 6-membered ring together with the nitrogen atom attached to R³⁴ andR³⁵, wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a —CHO group, a C₁-C₄alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group, a phenyl group, aphenyl group substituted with (Z)_(m) or an oxo group,

R³⁶ is a hydrogen atom, C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substitutedwith R³⁸, C₃-C₈ cycloalkyl, (C₃-C₈)cycloalkyl optionally substitutedwith R³⁸, E-2 to E-6, E-8, E-14 to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyloptionally substituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₈)alkynyloptionally substituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰, —C(O)OR⁴⁰,—C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹, —C(S)OR⁴⁰,—C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹, —S(O)₂R⁴⁰, —S(O)₂N(R⁴²)R⁴¹,Si(R^(14a))(R^(14b))R¹⁴, —P(O)(OR⁴³)₂ or —P(S)(OR⁴³)₂,

R³⁷ is C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substituted with R³⁸, C₃-C₈cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 toE-6, E-8, E-14 to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyl optionallysubstituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₈)alkynyl optionallysubstituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰, —C(O)OR⁴⁰, —C(O)C(O)OR⁴⁰,—C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹, —C(S)OR⁴⁰, —C(S)SR⁴⁰,—C(S)N(R⁴²)R⁴¹, —SH, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, phenylthio,phenylthio substituted with (Z)_(m), —P(O)(OR⁴³)₂ or —P(S)(OR⁴³)₂,

R³⁸ is a halogen atom, cyano, nitro, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, E-5, E-6, E-9, E-10, E-12, E-14, E-15, E-18, E-19, E-21,—OH, —OR⁴⁰, —OC(O)R³⁹, —OC(O)OR⁴⁰, —OC(O)N(R⁴²)R⁴¹, —OC(S)N(R⁴²)R⁴¹,—SH, —S(O)_(r)R⁴⁰, —SC(O)R³⁹, —SC(O)OR⁴⁰, —SC(O)N(R⁴²)R⁴¹,—SC(S)N(R⁴²)R⁴¹, —N(R⁴²)R⁴¹, —N(R⁴²)C(O)R⁴⁰, —N(R⁴²)C(O)SR⁴⁰,—N(R⁴²)C(O)N(R⁴²)R⁴¹, —N(R⁴²)C(S)N(R⁴²)R⁴¹, —N(R⁴²)S(O)₂R⁴⁰, —C(O)R³⁹,—C(O)OH, —C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(O)C(O)OR⁴⁰, —C(S)SR⁴⁰,—C(S)N(R⁴²)R⁴¹, —Si(R^(14a))(R^(14b))R¹⁴, —P(O)(OR⁴²)₂, —P(S)(OR⁴³)₂,—P(phenyl)₂, P(O)(phenyl)₂, phenyl, phenyl substituted with (Z)_(m), orD-1 to D-38,

R³⁹ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₁-C₄)alkyloptionally substituted with R⁴⁴, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl,E-5, E-6, E-14, E-15, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, cycloalkenyl,C₅-C₁₀ halocycloalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, phenyl,phenyl substituted with (Z)_(m), or D-1 to D-38,

R⁴⁰ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₁-C₄)alkyl optionally substitutedwith R⁴⁴, C₃-C₆ cycloalkyl, E-5, E-6, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl,C₃-C₈ alkynyl or phenyl,

R⁴¹ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₁-C₄)alkyloptionally substituted with R⁴⁴, C₃-C₆ cycloalkyl, E-5, E-6, E-14, C₂-C₈alkenyl, C₂-C₈ haloalkenyl, C₃-C₈ alkynyl, phenyl, phenyl substitutedwith (Z)_(m), D-1 to D-25 or D-27 to D-38, or may form theafter-mentioned ring together with R⁴²,

R⁴² is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl,C₃-C₆ alkenyl or C₃-C₆ alkynyl,

or R⁴² may form, together with R⁴¹, a C₂-C₅ alkylene chain to form a 3-to 6-membered ring together with the nitrogen atom attached to R⁴¹ andR⁴², wherein the alkylene chain may contain an oxygen atom, sulfur atomor nitrogen atom, and may optionally be substituted with a halogen atom,a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a —CHO group, a C₁-C₄alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group, a phenyl group or aphenyl group substituted with (Z)_(m),

R⁴³ is C₁-C₆ alkyl or C₁-C₆ haloalkyl,

R⁴⁴ is cyano, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, E-5, E-6, E-14,E-15, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, phenoxy, phenoxy substituted with(Z)_(m), C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, phenylthio, phenylthiosubstituted with (Z)_(m), C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylsulfonyl,phenylsulfonyl, phenylsulfonyl substituted with (Z)_(m), —N(R⁴⁶)R⁴⁵,C₁-C₄ alkylcarbonyl, C₁-C₄ haloalkylcarbonyl, C₁-C₄ alkoxycarbonyl,C₁-C₄ alkylaminocarbonyl, di(C₁-C₄ alkyl)aminocarbonyl, tri(C₁-C₄alkyl)silyl, phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38,

R⁴⁵ is a hydrogen atom, C₁-C₄ alkyl, C₁-C₄ alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄ alkoxycarbonyl, phenylcarbonyl orphenylcarbonyl substituted with (Z)_(m),

R⁴⁶ is a hydrogen atom or C₁-C₄ alkyl,

m is an integer of 1, 2, 3, 4 or 5,

n is an integer of 0, 1, 2, 3 or 4,

p is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,

r is an integer of 0, 1 or 2, and

t is an integer of 0 or 1.

Further, the present invention relates to all stereoisomers thereof, itsintermediate, and a pesticide containing it as an active ingredient.

Advantageous Effects of Invention

The compound of the present invention represented by the formula (I) andthe pesticide containing the compound as an active ingredient haveexcellent controlling effect on pests, especially fungi and nematodes inagricultural fields or zootechnical/hygienic fields, and have sufficientcontrolling effect on pests which have acquired resistance toconventional pesticides. Further, they have little harmful effect onnon-target organisms such as plants, mammals, fishes, useful insects andnatural enemies, show low persistence and are environmentally friendly.

Thus, the present invention can provide useful novel pesticides.

DESCRIPTION OF EMBODIMENT(S)

The oxime-substituted amide compounds of the present inventionrepresented by the formula (I) can have geometrical isomers such asE-isomers and Z-isomers, and the present invention covers both E-isomersand Z-isomers and mixtures containing them in any ratios. The compoundsof the present invention can have optically active isomers due to thepresence of one or more asymmetric carbon atoms depending on the typesof substituents in them, and the present invention covers any opticallyactive isomers and any racemates.

As a halogen atom herein, a fluorine atom, a chlorine atom, a bromineatom or an iodine atom may be mentioned. Herein, the expression “halo”also means such a halogen atom.

In the specific description of the substituents herein, the expression“n-” denotes “normal”, “i-” “iso”, “s-” “secondary”, “tert-” “tertiary”,and “Ph” “phenyl”.

The expression “C_(a)-C_(b) alkyl” herein means a linear or branchedhydrocarbon group containing from a to b carbon atoms such as a methylgroup, an ethyl group, a n-propyl group, an i-propyl group, a n-butylgroup, an i-butyl group, a s-butyl group, a tert-butyl group, a pentylgroup, a 1-ethylpropyl group, a 2,2-dimethylpropyl group or a hexylgroup, and those within the designated carbon number range are selected.

The expression “C_(a)-C_(b) haloalkyl” herein means a linear or branchedhydrocarbon group containing from a to b carbon atoms in which hydrogenatom(s) on carbon atom(s) are optionally substituted with halogenatom(s) which may be identical with or different from one another if twoor more halogen atoms are present, such as a fluoromethyl group, achloromethyl group, a bromomethyl group, an iodomethyl group, adifluoromethyl group, a dichloromethyl group, a trifluoromethyl group, achlorodifluoromethyl group, a trichloromethyl group, abromodifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group,a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group,a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a2,2,2-trichloroethyl group, a 2-bromo-2,2-difluoroethyl group, a1,1,2,2-tetrafluoroethyl group, a 2-chloro-1,1,2-trifluoroethyl group, apentafluoroethyl group, a 2,2-difluoropropyl group, a3,3,3-trifluoropropyl group, a 3-bromo-3,3-difluoropropyl group, a2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a2,2,2-trifluoro-1-(methyl)ethyl group, a2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, a2,2,3,4,4,4-hexafluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutylgroup or a nonafluorobutyl group, and those within the designated carbonnumber range are selected.

The expression “C_(a)-C_(b) cycloalkyl” herein means a cyclichydrocarbon group containing from a to b carbon atoms in the form of a3- to 10-membered monocyclic or polycyclic ring which may optionally besubstituted with an alkyl group as long as the number of carbon atomsdoes not exceed the designated carbon number range, such as acyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropylgroup, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, acyclopentyl group or a cyclohexyl group, and those within the designatedcarbon number range are selected.

The expression “C_(a)-C_(b) halocycloalkyl” herein means a cyclichydrocarbon group containing from a to b carbon atoms in the form of a3- to 10-membered monocyclic or polycyclic ring which may optionally besubstituted with an alkyl group as long as the number of carbon atomsdoes not exceed the designated carbon number range, in which hydrogenatom(s) on carbon atom(s) in a ring moiety and/or in a side chain areoptionally substituted with halogen atom(s) which may be identical withor different from one another if two or more halogen atoms are present,such as a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropylgroup, a 2,2-dibromocyclopropyl group, a2,2-difluoro-1-methylcyclopropyl group, a2,2-dichloro-1-methylcyclopropyl group, a2,2-dibromo-1-methylcyclopropyl group or a 2,2,3,3-tetrafluorocyclobutylgroup, and those within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) alkenyl” herein means a linear or branchedunsaturated hydrocarbon group containing from a to b carbon atoms andhaving one or more double bonds in the molecule such as a vinyl group, a1-propenyl group, a 2-propenyl group, a 1-methylethenyl group, a1-butenyl group, a 2-butenyl group, a 1-methyl-1-propenyl group, a2-methyl-1-propenyl group, a 2-methyl-2-propenyl group or a3-methyl-2-butenyl group, and those within the designated carbon atomrange are selected.

The expression “C_(a)-C_(b) haloalkenyl” herein means a linear orbranched unsaturated hydrocarbon group containing from a to b carbonatoms and having one or more double bonds in the molecule, in whichhydrogen atom(s) on carbon atom(s) are optionally substituted withhalogen atom(s) which may be identical with or different from oneanother if two or more halogen atoms are present, such as a2-fluorovinyl group, a 2-chlorovinyl group, a 1,2-dichlorovinyl group, a2,2-dichlorovinyl group, a 2-fluoro-2-propenyl group, a2-chloro-2-propenyl group, a 3-chloro-2-propenyl group, a3,3-difluoro-2-propenyl group, a 2,3-dichloro-2-propenyl group, a3,3-dichloro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl group, a2,3,3-trichloro-2-propenyl group, a 1-(trifluoromethyl)ethenyl group, a4,4-difluoro-3-butenyl group, a 3,4,4-trifluoro-3-butenyl group, a2,4,4,4-tetrafluoro-2-butenyl group or a3-chloro-4,4,4-trifluoro-2-butenyl group, and those within thedesignated carbon atom range are selected.

The expression “C_(a)-C_(b) cycloalkenyl” herein means a cyclicunsaturated hydrocarbon group containing from a to b carbon atoms andcontaining one or more endo- or exo-double bonds in the form of a 3- to10-membered monocyclic or polycyclic ring which may optionally besubstituted with an alkyl group as long as the number of carbon atomsdoes not exceed the designated carbon number range, such as a1-cyclopentenyl group, a 2-cyclopentenyl group, a 1-cyclohexenyl group,a 2-cyclohexenyl group or a bicyclo[2.2.1]-5-hepten-2-yl group, andthose within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) halocycloalkenyl” herein means a cyclicunsaturated hydrocarbon group containing from a to b carbon atoms andcontaining one or more endo- or exo-double bonds in the form of a 3- to10-membered monocyclic or polycyclic ring which may optionally besubstituted with an alkyl group as long as the number of carbon atomsdoes not exceed the designated carbon number range, in which hydrogenatom(s) on carbon atom(s) in the ring moiety and/or in the side chainare optionally substituted with halogen atom(s) which may be identicalwith or different from one another if two or more halogen atoms arepresent, such as a 2-fluoro-1-cyclopentenyl group, a2-chloro-1-cyclopentenyl group, a 3-chloro-2-cyclopentenyl group or a2-fluoro-1-cyclohexenyl group, and those within the designated carbonatom range are selected.

The expression “C_(a)-C_(b) alkylidene” herein means a linear orbranched hydrocarbon group containing from a to b carbon atoms whichattaches by a double bond, such as a methylidene group, an ethylidenegroup, a propylidene group or a 1-methylethylidene group, and thosewithin the designated carbon number range are selected.

The expression “C_(a)-C_(b) alkynyl” herein means a linear or branchedunsaturated hydrocarbon group containing from a to b carbon atoms andhaving one or more triple bonds in the molecule such as an ethynylgroup, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a2-pentynyl group or a 3-hexynyl group, and those within the designatedcarbon atom range are selected.

The expression “C_(a)-C_(b) haloalkynyl” herein means a linear orbranched unsaturated hydrocarbon group containing from a to b carbonatoms and having one or more triple bonds in the molecule, in whichhydrogen atom(s) on carbon atom(s) are optionally substituted withhalogen atom(s) which may be identical with or different from oneanother if two or more halogen atoms are present, such as a2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a3-chloro-2-propynyl group or a 3-bromo-2-propynyl group or a3-iodo-2-propynyl group, and those within the designated carbon numberrange are selected.

The expression “C_(a)-C_(b) alkoxy” herein means an alkyl-O— group inwhich the alkyl is a previously mentioned alkyl group containing from ato b carbon atoms, such as a methoxy group, an ethoxy group, an-propyloxy group, an i-propyloxy group, a n-butyloxy group, ani-butyloxy group, a s-butyloxy group, a tert-butyloxy group, a pentyloxygroup or a hexyloxy group, and those within the designated carbon atomrange are selected.

The expression “C_(a)-C_(b) haloalkoxy” herein means a haloalkyl-O—group in which the haloalkyl is a previously mentioned haloalkyl groupcontaining from a to b carbon atoms, such as a difluoromethoxy group, atrifluoromethoxy group, a chlorodifluoromethoxy group, abromodifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxygroup, a 2,2,2-trifluoroethoxy group, a 1,1,2,2,-tetrafluoroethoxygroup, a 2-chloro-1,1,2-trifluoroethoxy group or a1,1,2,3,3,3-hexafluoropropyloxy group, and those within the designatedcarbon atom range are selected.

The expression “C_(a)-C_(b) alkenyloxy” herein means an alkenyl-O— groupin which the alkenyl is a previously mentioned alkenyl group containingfrom a to b carbon atoms, such as a 2-propenyloxy group, a 2-butenyloxygroup, a 2-methyl-2-propenyloxy group or a 3-methyl-2-butenyloxy group,and those within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) alkylthio” herein means an alkyl-S— group inwhich the alkyl is a previously mentioned alkyl group containing from ato b carbon atoms, such as a methylthio group, an ethylthio group, an-propylthio group, an i-propylthio group, a n-butylthio group, ani-butylthio group, a s-butylthio group or a tert-butylthio group, andthose within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) haloalkylthio” herein means a haloalkyl-S—group in which the haloalkyl is a previously mentioned haloalkyl groupcontaining from a to b carbon atoms, such as a difluoromethylthio group,a trifluoromethylthio group, a chlorodifluoromethylthio group, abromodifluoromethylthio group, a 2,2,2-trifluoroethylthio group, a1,1,2,2-tetrafluoroethylthio group, a 2-chloro-1,1,2-trifluoroethylthiogroup, a pentafluoroethylthio group, a 1,1,2,3,3,3-hexafluoropropylthiogroup, a heptafluoropropylthio group, a1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio group or anonafluorobutylthio group, and those within the designated carbon atomrange are selected.

The expression “C_(a)-C_(b) alkylsulfinyl” herein means an alkyl-S(O)—group in which the alkyl is a previously mentioned alkyl groupcontaining from a to b carbon atoms, such as a methylsulfinyl group, anethylsulfinyl group, a n-propylsulfinyl group, an i-propylsulfinylgroup, a n-butylsulfinyl group, an i-butylsulfinyl group, as-butylsulfinyl group or a tert-butylsulfinyl group, and those withinthe designated carbon atom range are selected.

The expression “C_(a)-C_(b) haloalkylsulfinyl” herein means ahaloalkyl-S(O)— group in which the haloalkyl is a previously mentionedhaloalkyl group containing from a to b carbon atoms, such as adifluoromethylsulfinyl group, a trifluoromethylsulfinyl group, achlorodifluoromethylsulfinyl group, a bromodifluoromethylsulfinyl group,a 2,2,2-trifluoroethylsulfinyl group or a nonafluorobutylsulfinyl group,and those within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) alkylsulfonyl” herein means an alkyl-S(O)₂—group in which the alkyl is a previously mentioned alkyl groupcontaining from a to b carbon atoms, such as a methylsulfonyl group, anethylsulfonyl group, a n-propylsulfonyl group, an i-propylsulfonylgroup, a n-butylsulfonyl group, an i-butylsulfonyl group, as-butylsulfonyl group or a tert-butylsulfonyl group, and those withinthe designated carbon atom range are selected.

The expression “C_(a)-C_(b) haloalkylsulfonyl” herein means ahaloalkyl-S(O)₂— group in which the haloalkyl is a previously mentionedhaloalkyl group containing from a to b carbon atoms, such as adifluoromethylsulfonyl group, a trifluoromethylsulfonyl group, achlorodifluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group,a 2,2,2-trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonylgroup or a 2-chloro-1,1,2-trifluoroethylsulfonyl group, and those withinthe designated carbon atom range are selected.

The expression “C_(a)-C_(b) alkylamino” herein means an amino group inwhich either hydrogen atom is replaced by a previously mentioned alkylgroup containing from a to b carbon atoms, such as a methylamino group,an ethylamino group, a n-propylamino group, an i-propylamino group, an-butylamino group, an i-butylamino group or a tert-butylamino group,and those within the designated carbon atom range are selected.

The expression “di(C_(a)-C_(b) alkyl)amino” herein means an amino groupin which both hydrogen atoms are replaced by previously mentioned alkylgroups containing from a to b carbon atoms which may be identical withor different from each other, such as a dimethylamino group, anethyl(methyl)amino group, a diethylamino group, a di(n-propyl)aminogroup or a di(n-butyl)amino group, and those within the designatedcarbon atom range are selected.

The expression “C_(a)-C_(b) alkylimino” herein means an alkyl-N=group inwhich the alkyl is a previously mentioned alkyl group containing from ato b carbon atoms, such as a methylimino group, an ethylimino group, an-propylimino group, an i-propylimino group, a n-butylimino group, ani-butylimino group or a s-butylimino group, and those within thedesignated carbon atom range are selected.

The expression “C_(a)-C_(b) alkoxyimino” herein means an alkoxy-N=groupin which the alkoxy is a previously mentioned alkoxy group containingfrom a to b carbon atoms, such as a methoxyimino group, an ethoxyiminogroup, a n-propyloxyimino group, an i-propyloxyimino group or an-butyloxyimino group, and those within the designated carbon atom rangeare selected.

The expression “C_(a)-C_(b) alkylcarbonyl” herein means an alkyl-C(O)—group in which the alkyl is a previously mentioned alkyl groupcontaining from a to b carbon atoms, such as an acetyl group, apropionyl group, a butyryl group, an isobutyryl group, a valeryl group,an isovaleryl group, a 2-methylbutanoyl group or a pivaloyl group, andthose within the designated carbon atom range are selected.

The expression “C_(a)-C_(b) haloalkylcarbonyl” herein means ahaloalkyl-C(O)— group in which the haloalkyl is a previously mentionedhaloalkyl group containing from a to b carbon atoms, such as afluoroacetyl group, a chloroacetyl group, a difluoroacetyl group, adichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetylgroup, a bromodifluoroacetyl group, a trichloroacetyl group, apentafluoropropionyl group, a heptafluorobutanoyl group or a3-chloro-2,2-dimethylpropanoyl group, and those within the designatedcarbon atom range are selected.

The expression “C_(a)-C_(b) cycloalkylcarbonyl” herein means acycloalkyl-C(O)— group in which the cycloalkyl is a previously mentionedcycloalkyl group containing from a to b carbon atoms, such as acyclopropylcarbonyl group, a cyclobutylcarbonyl group, acyclopentylcarbonyl group, a 2,2-dimethylcyclopropylcarbonyl group or acyclohexylcarbonyl group, and those within the designated carbon atomrange are selected.

The expression “C_(a)-C_(b) alkoxycarbonyl” herein means analkyl-O—C(O)— group in which the alkyl is a previously mentioned alkylgroup containing from a to b carbon atoms, such as a methoxycarbonylgroup, an ethoxycarbonyl group, a n-propyloxycarbonyl group, ani-propyloxycarbonyl group, a n-butoxycarbonyl group, an i-butoxycarbonylgroup or a tert-butoxycarbonyl group, and those within the designatedcarbon atom range are selected.

The expression “C_(a)-C_(b) haloalkoxycarbonyl” herein means ahaloalkyl-O—C(O)-group in which the haloalkyl is a previously mentionedhaloalkyl group containing from a to b carbon atoms, such as achloromethoxycarbonyl group, a 2-chloroethoxycarbonyl group, a2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl groupor a 2,2,2-trichloroethoxycarbonyl group, and those within thedesignated carbon atom range are selected.

The expression “C_(a)-C_(b) alkylaminocarbonyl” herein means a carbamoylgroup in which either hydrogen atom is replaced by a previouslymentioned alkyl group containing from a to b carbon atoms, such as amethylcarbamoyl group, an ethylcarbamoyl group, a n-propylcarbamoylgroup, an i-propylcarbamoyl group, a n-butylcarbamoyl group, ani-butylcarbamoyl group, a s-butylcarbamoyl group or atert-butylcarbamoyl group, and those within the designated carbon atomrange are selected.

The expression “C_(a)-C_(b) haloalkylaminocarbonyl” herein means acarbamoyl group in which either hydrogen atom is replaced by apreviously mentioned haloalkyl group containing from a to b carbonatoms, such as a 2-fluoroethylcarbamoyl group, a 2-chloroethylcarbamoylgroup, a 2,2-difluoroethylcarbamoyl group or a2,2,2-trifluoroethylcarbamoyl group, and those within the designatedcarbon atom range are selected.

The expression “di(C_(a)-C_(b) alkyl)aminocarbonyl” herein means acarbamoyl group in which both hydrogen atoms are replaced by previouslymentioned alkyl groups containing from a to b carbon atoms which may beidentical with or different from each other, such as anN,N-dimethylcarbamoyl group, an N-ethyl-N-methylcarbamoyl group, anN,N-diethylcarbamoyl group, an N,N-di(n-propyl)carbamoyl group or anN,N-di(n-butyl)carbamoyl group, and those within the designated carbonatom range are selected.

The expression “di(C_(a)-C_(b) alkyl)aminosulfonyl” herein means asulfamoyl group in which both hydrogen atoms are replaced by previouslymentioned alkyl groups containing from a to b carbon atoms which may beidentical with or different from each other, such as anN,N-dimethylsulfamoyl group, an N-ethyl-N-methylsulfamoyl group, anN,N-diethylsulfamoyl group, an N,N-di(n-propyl)sulfamoyl group or anN,N-di(n-butyl)sulfamoyl group, and those within the designated carbonatom range are selected.

The expression “tri(C_(a)-C_(b) alkyl)silyl” herein means a silyl groupreplaced by previously mentioned alkyl groups containing from a to bcarbon atoms which may be identical with or different from one another,such as a trimethylsilyl group, a triethylsilyl group, atri(n-propyl)silyl group, an ethyldimethylsilyl group, an-propyldimethylsilyl group, a n-butyldimethylsilyl group, ani-butyldimethylsilyl group or a tert-butyldimethylsilyl group, and thosewithin the designated carbon atom range are selected.

The expression “C_(a)-C_(b) alkylsulfonyloxy” herein means analkylsulfonyl-O— group in which the alkylsulfonyl is a previouslymentioned alkylsulfonyl group containing from a to b carbon atoms, suchas a methylsulfonyloxy group, an ethylsulfonyloxy group, an-propylsulfonyloxy group or an i-propylsulfonyloxy group, and thosewithin the designated carbon atom range are selected.

The expression “C_(a)-C_(b) haloalkylsulfonyloxy” herein means ahaloalkylsulfonyl-O-group in which the haloalkylsulfonyl is a previouslymentioned haloalkylsulfonyl group containing from a to b carbon atoms,such as a difluoromethylsulfonyloxy group, a trifluoromethylsulfonyloxygroup, a chlorodifluoromethylsulfonyloxy group or abromodifluoromethylsulfonyloxy group, and those within the designatedcarbon atom range are selected.

The expression such as “C_(a)-C_(b) cycloalkyl(C_(d)-C_(e))alkyl”,“hydroxy(C_(d)-C_(e))alkyl”, “C_(a)-C_(b) alkoxy(C_(d)-C_(e))alkyl”,“C_(a)-C_(b) haloalkoxy(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)alkylthio(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)haloalkylthio(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)alkylsulfinyl(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)haloalkylsulfinyl(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)alkylsulfonyl(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)haloalkylsulfonyl(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)alkylamino(C_(d)-C_(e))alkyl”, “di(C_(a)-C_(b)alkyl)amino(C_(d)-C_(e))alkyl”, “cyano(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)alkoxycarbonyl(C_(d)-C_(e))alkyl”, “C_(a)-C_(b)haloalkoxycarbonyl(C_(d)-C_(e))alkyl”, “phenyl(C_(d)-C_(e))alkyl” or“phenyl(C_(d)-C_(e))alkyl substituted with (Z)_(m)” herein means apreviously mentioned alkyl group containing from d to e carbon atoms inwhich hydrogen atom(s) on carbon atom(s) are optionally substituted withpreviously mentioned optional C_(a)-C_(b) cycloalkyl group, C_(a)-C_(b)alkoxy group, C_(a)-C_(b) haloalkoxy group, C_(a)-C_(b) alkylthio group,C_(a)-C_(b) haloalkylthio group, C_(a)-C_(b) alkylsulfinyl group,C_(a)-C_(b) haloalkylsulfinyl group, C_(a)-C_(b) alkylsulfonyl group,C_(a)-C_(b) haloalkylsulfonyl group, C_(a)-C_(b) alkylamino group,di(C_(a)-C_(b) alkyl)amino group, C_(a)-C_(b) alkoxycarbonyl group,C_(a)-C_(b) haloalkoxycarbonyl group, hydroxy group, cyano group, phenylgroup or phenyl group substituted with (Z)_(m), and those within thedesignated carbon atom range are selected.

The expression such as “hydroxy(C_(d)-C_(e))cycloalkyl” or “C_(a)-C_(b)alkoxy(C_(d)-C_(e))cycloalkyl” herein means a previously mentionedcycloalkyl group containing from d to e carbon atoms in which hydrogenatom(s) on carbon atom(s) are optionally substituted with previouslymentioned optional C_(a)-C_(b) alkoxy group(s) or hydroxy group(s), andthose within the designated carbon atom range are selected.

The expression “phenyl(C_(a)-C_(b))alkynyl” herein means a previouslymentioned alkynyl group containing from a to b carbon atoms in whichhydrogen atom(s) on carbon atom(s) are optionally substituted withphenyl group(s), and those within the designated carbon atom range areselected.

The expression such as “(C_(a)-C_(b)) alkyl optionally substituted withR⁶”, “(C_(a)-C_(b)) alkyl optionally substituted with R¹⁸”,“(C_(a)-C_(b)) alkyl optionally substituted with R¹⁹”, “(C_(a)-C_(b))alkyl optionally substituted with R²⁸”, “(C_(a)-C_(b)) alkyl optionallysubstituted with R³⁸” or “(C_(a)-C_(b)) alkyl optionally substitutedwith R⁴⁴” herein means a previously mentioned alkyl group containingfrom a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) areoptionally substituted with optional R⁶, R¹⁸, R¹⁹, R²⁸, R³⁸ or R⁴⁴, andthose within the designated carbon atom range are selected. When thereare two or more R⁶'s, R¹⁸'s, R¹⁹'s, R²⁸'s, R³⁸'s or R⁴⁴'s on a(C_(a)-C_(b)) alkyl group, each R⁶, R¹⁸, R¹⁹, R²⁸, R³⁸ or R⁴⁴ may beidentical with or different from one another.

The expression such as “(C_(a)-C_(b)) cycloalkyl optionally substitutedwith R⁶”, “(C_(a)-C_(b)) cycloalkyl optionally substituted with R²⁸” or“(C_(a)-C_(b)) cycloalkyl optionally substituted with R³⁸” herein meansa previously mentioned cycloalkyl group containing from a to b carbonatoms in which hydrogen atom(s) on carbon atom(s) in the ring moietyand/or in the side chain are optionally substituted with optional R⁶,R²⁸ or R³⁸, and those within the designated carbon atom range areselected. When there are two or more R⁶'s, R²⁸'s or R³⁸'s on a(C_(a)-C_(b)) cycloalkyl group, each R⁶, R²⁸ or R³⁸ may be identicalwith or different from one another.

The expression such as “(C_(a)-C_(b)) alkenyl optionally substitutedwith R⁶”, “(C_(a)-C_(b)) alkenyl optionally substituted with R²⁸” or“(C_(a)-C_(b)) alkenyl optionally substituted with R³⁸” herein means apreviously mentioned alkenyl group containing from a to b carbon atomsin which hydrogen atom(s) on carbon atom(s) are optionally substitutedwith optional R⁶, R²⁸ or R³⁸, and those within the designated carbonatom range are selected. When there are two or more R⁶'s, R²⁸'s or R³⁸'son a (C_(a)-C_(b)) alkenyl group, each R⁶, R²⁸ or R³⁸ may be identicalwith or different from one another.

The expression such as “(C_(a)-C_(b)) alkynyl optionally substitutedwith R⁶”, “(C_(a)-C_(b)) alkynyl optionally substituted with R²⁸” or“(C_(a)-C_(b)) alkynyl optionally substituted with R³⁸” herein means apreviously mentioned alkynyl group containing from a to b carbon atomsin which hydrogen atom(s) on carbon atom(s) are optionally substitutedwith optional R⁶, R²⁸ or R³⁸, and those within the designated carbonatom range are selected. When there are two or more R⁶'s, R²⁸'s or R³⁸'son a (C_(a)-C_(b)) alkynyl group, each R⁶, R²⁸ or R³⁸ may be identicalwith or different from one another.

The expression “R³ may form, together with R², a C₂-C₅ alkylene chain toform a 3- to 6-membered ring together with the carbon atom attached toR² and R³, wherein the alkylene chain may contain an oxygen atom, sulfuratom or nitrogen atom” is specifically exemplified by a cyclopropanering, a cyclobutane ring, a cyclopentane ring, a tetrahydrofuran ring, atetrahydrothiophene ring, a pyrrolidine ring, a cyclohexane ring, atetrahydropyran ring, a tetrahydrothiopyran ring, a piperidine ring, acycloheptane ring, an oxepane ring, a thiepane ring, an azepane ring orthe like, and those within the designated carbon atom range areselected.

The expression such as “R⁹ may form, together with R⁸, a C₂-C₆ alkylenechain to form a 3- to 7-membered ring together with the nitrogen atomattached to R⁸ and R⁹, wherein the alkylene chain may contain an oxygenatom, sulfur atom or nitrogen atom, and may optionally be substitutedwith an oxo group or a thioxo group”, “R²⁵ and R²⁴ together may form aC₄-C₅ alkylene chain to form a 5- to 6-membered ring together with thenitrogen atom attached to R²⁴ and R²⁵, wherein the alkylene chain maycontain an oxygen atom, sulfur atom or nitrogen atom, and may optionallybe substituted with an oxo group or a thioxo group”, “R³⁰ may form,together with R²⁹, a C₂-C₆ alkylene chain to form a 3- to 7-memberedring together with the nitrogen atom attached to R²⁹ and R³⁰, whereinthe alkylene chain may contain an oxygen atom, sulfur atom or nitrogenatom, and may optionally be substituted with an oxo group or a thioxogroup” or “R³⁵ may form, together with R³⁴, a C₂-C₅ alkylene chain toform a 3- to 6-membered ring together with the nitrogen atom attached toR³⁴ and R³⁵, wherein the alkylene chain may contain an oxygen atom,sulfur atom or nitrogen atom, and may optionally be substituted with anoxo group” is specifically exemplified by aziridine, azetidine,azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine,oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one,thiazolidine-2-thione, imidazolidine, imidazolidin-2-one,imidazolidine-2-thione, piperidine, piperidin-2-one,piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one,2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine,2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one,2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine,thiomorpholine-1-oxide, thiomorpholine-1,1-dioxide,perhydropyrimidine-2-one, piperazine, homopiperidine,homopiperidin-2-one, heptamethyleneimine or the like, and those withinthe designated carbon atom range are selected.

The expression such as “R¹³ may form, together with R¹², a C₂-C₆alkylene chain to form a 3- to 7-membered ring together with thenitrogen atom attached to R¹² and R¹³, wherein the alkylene chain maycontain an oxygen atom, sulfur atom or nitrogen atom”, “R²³ may form,together with R²², a C₂-C₆ alkylene chain to form a 3- to 7-memberedring together with the nitrogen atom attached to R²² and R²³, whereinthe alkylene chain may contain an oxygen atom, sulfur atom or nitrogenatom”, “R²⁷ may form, together with R²⁶, a C₄-C₇ alkylene chain to forma 5- to 8-membered ring together with the nitrogen atom attached to R²⁶and R²⁷, wherein the alkylene chain may contain an oxygen atom or sulfuratom” or “R⁴² may form, together with R⁴¹, a C₂-C₅ alkylene chain toform a 3- to 6-membered ring together with the nitrogen atom attached toR⁴¹ and R⁴², wherein the alkylene chain may contain an oxygen atom,sulfur atom or nitrogen atom” is specifically exemplified by aziridine,azetidine, pyrrolidine, oxazolidine, thiazolidine, imidazolidine,piperidine, morpholine, thiomorpholine, thiomorpholine-1-oxide,thiomorpholine-1,1-dioxide, piperazine, homopiperidine,heptamethyleneimine or the like, and those within the designated carbonatom range are selected.

The expression such as “R^(9a) may form, together with R^(8a), a C₄-C₆alkylene chain to form a 5- to 7-membered ring together with the carbonatom attached to R^(8a) and R^(9a), wherein the alkylene chain maycontain an oxygen atom or sulfur atom” or “R^(25a) may form, togetherwith R^(24a), a C₃-C₅ alkylene chain to form a 4- to 6-membered ringtogether with the carbon atom attached to R^(24a) and R^(25a), whereinthe alkylene chain may contain an oxygen atom, sulfur atom or nitrogenatom” is specifically exemplified by cyclopentylidene,tetrahydrofuran-3-ylidene, tetrahydrothiophen-3-ylidene,cyclohexylidene, tetrahydropyran-3-ylidene, tetrahydropyran-4-ylidene,tetrahydrothiopyran-3-ylidene, tetrahydrothiopyran-4-ylidene or thelike, and those within the designated carbon atom range are selected.

As the preferred range of the substituent represented by G¹ in thecompounds which fall within the present invention, the following setsmay, for example, be mentioned.

G¹-I: G¹-1 [wherein X¹ is a bromine atom, an iodine atom, methyl,difluoromethyl or trifluoromethyl, and X², X³, X⁴ and X⁵ are hydrogenatoms].

G¹-II: G¹-1 [wherein X¹ is a chlorine atom, and X², X³, X⁴ and X⁵ arehydrogen atoms].

G¹-III: G¹-2 [wherein X¹ is a halogen atom, methyl or trifluoromethyl,and X³, X⁴ and X⁵ are hydrogen atoms].

G¹-IV: G¹-3 [wherein X¹ is a halogen atom or trifluoromethyl, and X², X³and X⁴ are hydrogen atoms].

G¹-V: G¹-7 [wherein X¹ is trifluoromethyl, and X³ and X⁴ are hydrogenatoms].

G¹-VI: G¹-11 [wherein X¹ is a halogen atom, methyl or trifluoromethyl,and X³ and X⁴ are hydrogen atoms].

G¹-VII: G¹-12 [wherein X¹ is a halogen atom or trifluoromethyl, and X²and X³ are hydrogen atoms].

G¹-VIII: G¹-16 [wherein X¹ is trifluoromethyl, X² and X⁴ are hydrogenatoms, and R⁵ is methyl].

G¹-IX: G¹-27 [wherein X¹ is difluoromethyl or trifluoromethyl, X² is ahydrogen atom, and R⁵ is methyl].

G¹-X: G¹-33 [wherein X¹ is difluoromethyl or trifluoromethyl, and X³ ismethyl].

G¹-XI: G¹-1 [wherein X¹ is nitro, and X², X³, X⁴ and X⁵ are hydrogenatoms].

G¹-XII: G¹-1 [wherein X¹ is trifluoromethyl, X² and X³ are hydrogenatoms, X⁴ is a halogen atom, and X⁵ is a hydrogen atom].

G¹-XIII: G¹-9 [wherein X¹ is methyl or trifluoromethyl, X² is a hydrogenatom, and X³ is methyl].

G¹-XIV: G¹-27 [wherein X¹ is a halogen atom or trifluoromethyl, X² is ahalogen atom, and R⁵ is methyl].

G¹-XV: G¹-32 [wherein X¹ and X³ are methyl].

G¹-XVI: G¹-50 [wherein X¹ is trifluoromethyl, and r is 0].

G¹-XVII: G¹-1 [wherein X¹ is a fluorine atom, cyano, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio or phenyl, and X², X³, X⁴ and X⁵ arehydrogen atoms].

G¹-XVIII: G¹-1 [wherein X¹ is a halogen atom, methyl or trifluoromethyl,X² is a hydrogen atom or a halogen atom, X³ and X⁴ are hydrogen atoms,and X⁵ is a hydrogen atom or a halogen atom].

G¹-XIX: G¹-2 [wherein X¹ is a halogen atom, X³ is a hydrogen atom, X⁴ istrifluoromethyl, and X⁵ is a hydrogen atom].

G¹-XX: G¹-4 [wherein X¹ is trifluoromethyl, and X², X³ and X⁵ arehydrogen atoms].

G¹-XXI: G¹-8 [wherein X¹ is a halogen atom or methyl, and X³ and X⁴ arehydrogen atoms].

G¹-XXII: G¹-9 [wherein X¹ is trifluoromethyl, X² is a hydrogen atom, andX³ is phenyl].

G¹-XXIII: G¹-13 [wherein X¹ is a halogen atom, and X² and X⁴ arehydrogen atoms].

G¹-XXIV: G¹-20 [wherein X¹ is trifluoromethyl, and X² is a hydrogenatom].

G¹-XXV: G¹-30 [wherein X¹ is trifluoromethyl, and X³ is methyl].

G¹-XXVI: G¹-33 [wherein X¹ and X³ are trifluoromethyl].

G¹-XXVII: G¹-44 [wherein X¹ is trifluoromethyl, and R⁵ is C₁-C₄ alkyl].

G¹-XXVIII: G¹-1 [wherein X¹ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆cycloalkyl, C₄ haloalkylthio, —NH₂ or D-3, X², X³, X⁴ and X⁵ arehydrogen atoms, and n is 0].

G¹-XXIX: G¹-2 [wherein X¹ is difluoromethyl, and X³, X⁴ and X⁵ arehydrogen atoms].

G¹-XXX: G¹-3 [wherein X¹ is methyl, and X², X³ and X⁴ are hydrogenatoms].

G¹-XXXI: G¹-5 [wherein X¹ is trifluoromethyl, and X⁴ and X⁵ are hydrogenatoms].

G¹-XXXII: G¹-7 [wherein X¹ is a halogen atom or methyl, and X³ and X⁴are hydrogen atoms].

G¹-XXXIII: G¹-8 [wherein X¹ is trifluoromethyl, and X³ and X⁴ arehydrogen atoms].

G¹-XXXIV: G¹-9 and G¹-12 [wherein X¹ is difluoromethyl, and X² and X³are hydrogen atoms].

G¹-XXXV: G¹-10 and G¹-13 [wherein X¹ is difluoromethyl ortrifluoromethyl, and X² and X⁴ are hydrogen atoms].

G¹-XXXVI: G¹-11 [wherein X¹ is difluoromethyl, and X³ and X⁴ arehydrogen atoms].

G¹-XXXVII: G¹-16 [wherein X¹ is difluoromethyl or trifluoromethyl, X²and X⁴ are hydrogen atoms, and R⁵ is C₁-C₄ alkyl].

G¹-XXXVIII: G¹-19 and G¹-23 [wherein X¹ is difluoromethyl ortrifluoromethyl, and X² is a hydrogen atom].

G¹-XXXIX: G¹-27 [wherein X¹ is a halogen atom, C₁-C₄ alkyl, C₂-C₄haloalkyl or C₁-C₄ alkoxy, X² is a hydrogen atom, a fluorine atom or achlorine atom, and R⁵ is C₁-C₄ alkyl].

G¹-XL: G¹-27 [wherein X¹ is C₁-C₄ alkyl or C₁-C₄ haloalkyl, X² is ahydrogen atom, and R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₃-C₆cycloalkyl].

G¹-XLI: G¹-31 [wherein X¹ is trifluoromethyl, and X³ is a halogen atomor methyl].

G¹-XLII: G¹-32 [wherein X¹ is a halogen atom, difluoromethyl ortrifluoromethyl, and X³ is a hydrogen atom or methyl].

G¹-XLIII: G¹-33 [wherein X¹ is a halogen atom, methyl, difluoromethyl ortrifluoromethyl, and X³ is a hydrogen atom, a halogen atom, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy or —NH₂].

G¹-XLIV: G¹-41 and G¹-43 [wherein X¹ is trifluoromethyl].

G¹-XLV: G¹-45, G¹-46, G¹-49 and G¹-51 [wherein X¹ is methyl ortrifluoromethyl].

G¹-XLVI: G¹-50 [wherein X¹ is methyl or trifluoromethyl, and r is aninteger of from 0 to 2].

Among them, as the scope of the substituent represented by G¹, morepreferred are G¹-I to G¹-XVI, G¹-XXIX, G¹-XXX, G¹-XXXII to G¹-XXXVII andG¹-XLII, particularly preferred are G¹-I to G¹-X.

As the preferred range of the substituent represented by G² in thecompounds which fall within the present invention, the following setsmay, for example, be mentioned.

G²-I: G²-1 [wherein Y¹ is a halogen atom, Y² is a hydrogen atom, Y³ is ahalogen atom or methyl, and Y⁴ and Y⁵ are hydrogen atoms].

G²-II: G²-2 [wherein Y¹ is a halogen atom, Y² is a hydrogen atom or ahalogen atom, Y³ is a halogen atom, cyano, trifluoromethyl, C₁-C₄haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₆ alkynyl, cyclopropylethynyl,trimethylsilylethynyl or phenylethynyl, Y⁴ is a hydrogen atom or ahalogen atom, R¹⁰ is methyl, and R¹¹ is methyl or ethyl].

G²-III: G²-1 [wherein Y¹ and Y² are hydrogen atoms, Y³ is a halogen atomor methyl, and Y⁴ and Y⁵ are hydrogen atoms].

G²-IV: G²-1 [wherein Y¹ is a hydrogen atom, Y² and Y³ together may form—CH═CHCH═CH— to form a 6-membered ring together with the carbon atomsattached to Y² and Y³, and Y⁴ and Y⁵ are hydrogen atoms].

G²-V: G²-1 [wherein Y¹ is a halogen atom, methyl, trifluoromethyl ormethoxy, Y² is a hydrogen atom or a halogen atom, Y³ is a hydrogen atom,a halogen atom, methyl, trifluoromethyl, C₁-C₄ alkoxy, —C(R¹⁰)═NOR¹¹,C₂-C₄ alkenyl, phenyl or D-7, Y⁴ is a hydrogen atom or a halogen atom,Y⁵ is a hydrogen atom or a halogen atom, Z is trifluoromethyl, R¹⁰ ismethyl, R¹¹ is methyl or ethyl, and n is 1].

G²-VI: G²-2 [wherein Y¹ is a halogen atom, Y² is a hydrogen atom, Y³ ismethyl, C₁-C₄ alkoxy, C₂-C₄ alkenyl, (C₂-C₆)alkynyl substituted with R⁶,D-3 or D-7, Y⁴ is a hydrogen atom, R⁶ is a halogen atom, C₃-C₆cycloalkyl, —OH, trimethylsilyl or phenyl, and n is 0].

G²-VII: G²-2 [wherein Y¹ is a halogen atom, Y² is cyano, Y³ is a halogenatom, and Y⁴ is a hydrogen atom].

G²-VIII: G²-6 [wherein Y¹ and Y³ are halogen atoms, and Y⁴ is a hydrogenatom].

G²-IX: G²-9 [wherein Y¹ is a halogen atom, Y² is a hydrogen atom or ahalogen atom, and Y³ is a halogen atom].

G²-X: G²-10 [wherein Y¹ is a halogen atom, Y³ is a hydrogen atom or ahalogen atom, and Y⁴ is a hydrogen atom].

G²-XI: G²-1 [wherein Y¹ and Y² are hydrogen atoms, Y³ is C₂-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy, phenoxy or phenyl, and Y⁴ and Y⁵ arehydrogen atoms].

G²-XII: G²-1 [wherein Y¹ is a hydrogen atom, Y² is a halogen atom orC₁-C₄ alkoxy, Y³ is a hydrogen atom or a halogen atom, Y⁴ is a hydrogenatom, a halogen atom or trifluoromethyl, and Y⁵ is a hydrogen atom].

G²-XIII: G²-1 [wherein Y¹ is a halogen atom, E-9 or —C(R¹⁰)═NOR¹¹, Y² isa hydrogen atom, or Y² may form, together with Y¹, —CH═CHCH═CH— to forma 6-membered ring together with the carbon atoms attached to Y¹ and Y²,Y³ is a hydrogen atom, a halogen atom, cyano, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, —C(O)R¹⁰, M-7, phenyl substitutedwith (Z)_(m), D-3 or D-7, Y⁴ is a hydrogen atom or trifluoromethyl, Y⁵is a hydrogen atom, Z is trifluoromethoxy, R¹⁰ is a hydrogen atom orC₁-C₄ alkyl, R¹¹ is C₁-C₄ alkyl, R¹⁷ is methyl, m is 1, n is 0, and p isan integer of from 0 to 2.

G²-XIV: G²-2 [wherein Y¹ is a hydrogen atom, a halogen atom,trifluoromethyl or methoxy, Y² is a hydrogen atom, Y³ is a halogen atom,C₁-C₄ haloalkyl, C₁-C₄ alkoxymethyl, —OR⁷ or D-22, Y⁴ is a hydrogen atomor methoxy, R⁷ is phenyl or phenyl substituted with (Z)_(m), Z is ahalogen atom, m is 1, and n is 0].

G²-XV: G²-3 [wherein Y¹ is a halogen atom, each of Y³ and Y⁴ isindependently a hydrogen atom or a halogen atom, and Y⁵ is a hydrogenatom].

G²-XVI: G²-11 [wherein Y¹ is a halogen atom, Y² is C₁-C₄ alkoxy, and R⁵is methyl].

G²-XVII: G²-12 [wherein Y¹ is trifluoromethyl, Y⁴ is a hydrogen atom,and R⁵ is methyl].

G²-XVIII: G²-17 [wherein Y¹ and Y³ are halogen atoms].

G²-XIX: G²-1 [wherein Y¹ is a hydrogen atom, Y² is a hydrogen atom, ahalogen atom, methyl, trifluoromethyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy orphenoxy, Y³ is a hydrogen atom, a halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxyor C₁-C₄ haloalkylthio, or Y³ may form, together with Y², —OCH₂O—,—OCH₂CH₂O— or —CH═CHCH═CH— to form a 5-membered ring or a 6-memberedring together with the carbon atoms attached to Y² and Y³, whereinhydrogen atoms on the respective ring-constituting carbon atoms mayoptionally be substituted with a halogen atom or methyl, Y⁴ is ahydrogen atom, a halogen atom, methyl or trifluoromethyl, and Y⁵ is ahydrogen atom].

G²-XX: G²-1 [wherein Y¹ is a halogen atom, methyl or trifluoromethyl, Y²is a hydrogen atom, Y³ is cyano, nitro, —OR⁷, —S(O)_(r)R⁷,—C(R¹⁰)═NOR¹¹, —C(O)NH₂, —C(S)NH₂, C₂-C₆ alkynyl or (C₂-C₆)alkynylsubstituted with R⁶, Y⁴ and Y⁵ are hydrogen atoms, R⁶ is a halogen atom,C₃-C₆ cycloalkyl, —OH, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl or —Si(R^(14a))(R^(14b))R¹⁴, R⁷ isC₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₃-C₄ haloalkynyl, phenyl or phenylsubstituted with (Z)_(m), R¹⁰ is a hydrogen atom or C₁-C₄ alkyl, R¹¹ isC₁-C₄ alkyl, R¹⁴ is C₁-C₄ alkyl or phenyl, each of R^(14a) and R^(14b)is independently C₁-C₄ alkyl, Z is a halogen atom, m is 1, and r is aninteger of from 0 to 2].

G²-XXI: G²-1 [wherein Y¹ is a halogen atom, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxymethyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, phenoxyor C₁-C₄ alkylthio, Y² is a hydrogen atom, methyl or methoxy, or Y² mayform, together with Y¹, —OCH₂O— or —OCH₂CH₂O—, to form a 5-membered ringor a 6-membered ring together with the carbon atoms attached to Y¹ andY², wherein hydrogen atoms on the respective ring-constituting carbonatoms may optionally be substituted with a halogen atom or methyl, Y³ isa hydrogen atom, a halogen atom, cyano, nitro, methyl ortrifluoromethyl, or Y³ may form, together with Y², —OCH₂O— or —OCH₂CH₂O—to form a 5-membered ring or a 6-membered ring together with the carbonatoms attached to Y² and Y³, wherein hydrogen atoms on the respectivering-constituting carbon atoms may optionally be substituted with ahalogen atom or methyl, and Y⁴ and Y⁵ are hydrogen atoms].

G²-XXII: G²-1 [wherein Y¹ is a halogen atom, methyl or methoxy, Y² is ahydrogen atom, Y³ is a hydrogen atom, a halogen atom, methyl ortrifluoromethyl, Y⁴ is a halogen atom, methyl or methoxy, or Y⁴ mayform, together with Y³, —OCH₂O— or —OCH₂CH₂O—, to form a 5-membered ringor a 6-membered ring together with the carbon atoms attached to Y³ andY⁴, wherein hydrogen atoms on the respective ring-constituting carbonatoms may optionally be substituted with a halogen atom or methyl, andY⁵ is a hydrogen atom].

G²-XXIII: G²-1 [wherein Y¹ is a halogen atom, methyl or trifluoromethyl,Y² is a hydrogen atom or a halogen atom, Y³ is a hydrogen atom, ahalogen atom, C₁-C₄ alkyl, trifluoromethyl or methoxy, Y⁴ is a hydrogenatom, and Y⁵ is a halogen atom or methyl].

G²-XXIV: G²-2 [wherein Y¹ is cyano, nitro, difluoromethoxy,trifluoromethoxy or methylthio, Y² is a hydrogen atom, Y³ is a halogenatom, C₁-C₄ alkyl or trifluoromethyl, and Y⁴ is a hydrogen atom].

G²-XXV: G²-2 [wherein Y¹ is a halogen atom, methyl or trifluoromethyl,Y² is cyano, methyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or C₁-C₄ alkylthio,Y³ is a halogen atom, methyl or trifluoromethyl, and Y⁴ is a hydrogenatom].

G²-XXVI: G²-2 [wherein Y¹ is a halogen atom, methyl or trifluoromethyl,Y² is a hydrogen atom, Y³ is a halogen atom, cyano, nitro, methyl,difluoromethyl, trifluoromethyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, —N(R⁹)R⁸, —C(R¹⁰)═NOR¹¹, M-3, —C(O)NH₂, —C(S)NH₂,—SO₂N(CH₃)₂, C₂-C₆ alkynyl, (C₂-C₆)alkynyl substituted with R⁶, D-11,D-28 or D-29, Y⁴ is a hydrogen atom, R⁶ is a halogen atom, C₃-C₆cycloalkyl, hydroxy(C₃-C₆)cycloalkyl, C₃-C₄ alkenyl, C₅-C₆ cycloalkenyl,—OH, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, alkylsulfonyl, —Si(R^(14a))(R^(14b))R¹⁴, phenyl, phenylsubstituted with (Z)_(m), D-1, D-2, D-4, D-12 or D-32, R⁸ and R⁹together may form a C₄-C₅ alkylene chain to form a 5- to 6-membered ringtogether with the nitrogen atom attached to R⁸ and R⁹, wherein thealkylene chain may contain an oxygen atom or sulfur atom, R¹⁰ is ahydrogen atom or C₁-C₄ alkyl, R¹¹ is C₁-C₄ alkyl, R¹⁴ is C₁-C₄ alkyl orphenyl, each of R^(14a) and R^(14b) is independently a C₁-C₄ alkyl, R¹⁷is C₁-C₄ alkyl, Z is a halogen atom or C₁-C₄ alkyl, m is an integer of 1or 2, n is 0, and p is an integer of from 0 to 2].

G²-XXVII: G²-3 [wherein Y¹ is a halogen atom or methyl, Y³ is a halogenatom, methyl, trifluoromethyl or methoxy, Y⁴ is a halogen atom or cyano,and Y⁵ is a hydrogen atom].

G²-XXVIII: G²-4 [wherein Y¹ is a halogen atom or methyl, Y² is ahydrogen atom, Y³ is a halogen atom or methoxy, and Y⁵ is a hydrogenatom].

G²-XXIX: G²-5 [wherein Y¹ is a halogen atom, methyl, difluoromethyl ortrifluoromethyl, Y² is a hydrogen atom, and Y³ is a halogen atom,methyl, trifluoromethyl or methoxy].

G²-XXX: G²-6 [wherein each of Y¹ and Y³ is independently a halogen atomor methyl, and Y⁴ is a hydrogen atom or methyl].

G²-XXXI: G²-7 [wherein Y¹, Y² and Y³ are halogen atoms].

G²-XXXII: G²-9 [wherein Y¹ is a halogen atom or methyl, Y² is a hydrogenatom, a halogen atom or methyl, Y³ is a halogen atom, or Y³ may form,together with Y², —CH═CHCH═CH— to form a 6-membered ring together withthe carbon atoms attached to Y² and Y³, wherein hydrogen atoms on therespective ring-constituting carbon atoms may optionally be substitutedwith a halogen atom].

G²-XXXIII: G²-10 [wherein Y¹ is methyl, Y³ is a hydrogen atom, a halogenatom or methyl, and Y⁴ is a hydrogen atom].

G²-XXXIV: G²-10 [wherein Y¹ is a hydrogen atom or a halogen atom, Y³ isa halogen atom, Y⁴ is a halogen atom, or Y⁴ may form, together with Y³,—CH₂CH₂CH₂CH₂— or —CH═CHCH═CH— to form a 6-membered ring together withthe carbon atoms attached to Y³ and Y⁴, wherein hydrogen atoms on therespective ring-constituting carbon atoms may optionally be substitutedwith a halogen atom].

G²-XXXV: G²-14 [wherein Y¹ is methyl, and Y³ is trifluoromethyl].

G²-XXXVI: G²-16 and G²-17 [wherein Y¹ is methyl, and Y³ is a halogenatom or trifluoromethyl].

Among them, as the scope of the substituent represented by G², morepreferred are G²-I to G²-X, G²-XX, G²-XXVIII, G²-XXIX and G²-XXX,particularly preferred are G²-I and G²-II.

In the compounds which fall within the present invention, thesubstituent represented by W may be an oxygen atom or a sulfur atom, andW is preferably an oxygen atom.

As the preferred range of the substituent represented by R¹ in thecompounds which fall within the present invention, the following setsmay, for example, be mentioned.

R¹-I: C₁-C₆ alkyl, (C₁-C₄)alkyl substituted with R¹⁸ [wherein R¹⁸ isC₃-C₆ cycloalkyl or trimethylsilyl], C₃-C₆ cycloalkyl, C₃-C₆ alkenyl andC₃-C₆ alkynyl.

R¹-II: C₁-C₄ haloalkyl, (C₁-C₄)alkyl substituted with R¹⁸ [wherein R¹⁸is phenyl, phenyl substituted with (Z)_(m) or D-32, Z is a halogen atom,cyano, nitro, methyl, trifluoromethyl or trifluoromethoxy, when m is aninteger of at least 2, the respective Z's may be identical with ordifferent from one another, m is an integer of from 1 to 3, and n is 1],and C₃-C₄ haloalkenyl.

R¹-III: (C₁-C₄)alkyl substituted with R¹⁸ [wherein R¹⁸ is cyano, E-5,C₁-C₄ alkoxy, C₁-C₄ alkylthio, —C(R³²)═NOR³³, D-5 or D-10, R³² ismethyl, R³³ is methyl or ethyl, Z is a halogen atom or methyl, n is aninteger of 0 or 1, and p is 0], and phenyl.

R¹-IV: (C₁-C₄)alkyl substituted with R¹⁸ [wherein R¹⁸ is phenylsubstituted with (Z)_(m) or D-32, Z is a halogen atom, C₁-C₄ alkyl,methoxy, trifluoromethylthio or phenyl, when m and n are 2, the two Z'smay be identical with or different from each other, and when there aretwo neighboring Z's, the two neighboring Z's may form —CH═CH—CH═CH— toform a 6-membered ring together with the carbon atoms attached to theZ's, m is an integer of 1 or 2, and n is an integer of from 0 to 2].

R¹-V: (C₁-C₄)alkyl substituted with R¹⁸ [wherein R¹⁸ is E-9,—C(R³²)═NOR³³, M-4, C₁-C₄ alkoxycarbonyl, C₁-C₄ haloalkylaminocarbonylor D-1, R³² is a hydrogen atom or C₁-C₄ alkyl, R³³ is C₁-C₄ alkyl, Z ismethyl or trifluoromethyl, n is 1, and p is 0], E-2 [wherein p is 0] andE-14 [wherein p is 0].

R¹-VI: C₃-C₆ halocycloalkyl and C₃-C₄ haloalkynyl.

R¹-VII: E-3 [wherein p is 0, and r is an integer of from 0 to 2], E-4[wherein R¹⁶ is —C(O)R¹⁰ or —C(O)OR¹¹, R¹⁰ is a hydrogen atom, C₁-C₄alkyl or cyclopropyl, R¹¹ is C₁-C₄ alkyl or C₁-C₄ haloalkyl, and p is0], E-5 [wherein p is 0], E-6 [wherein p is 0, and r is an integer offrom 0 to 2], E-8 [wherein R¹⁶ is —C(O)R¹⁶ or —C(O)OR¹¹, R¹⁰ is ahydrogen atom, C₁-C₄ alkyl or cyclopropyl, R¹¹ is C₁-C₄ alkyl or C₁-C₄haloalkyl, and p is 0], E-15 [wherein p is 0, and r is an integer offrom 0 to 2], and E-17 [wherein R¹⁶ is —C(O)R¹⁰ or —C(O)OR¹¹, R¹⁰ is ahydrogen atom, C₁-C₄ alkyl or cyclopropyl, R¹¹ is C₁-C₄ alkyl or C₁-C₄haloalkyl, and p is 0].

R¹-VIII: (C₁-C₄)alkyl optionally substituted with R¹⁸ [wherein R¹⁸ is ahalogen atom, C₃-C₆ halocycloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy orC₁-C₄ alkylthio].

R¹-IX: (C₁-C₄)alkyl optionally substituted with R¹⁸ [wherein R¹⁸ is ahalogen atom, E-2 to E-4, E-6, E-8, M-3, —C(R³²)═NOR³³, —C(O)NH₂ or—C(S)NH₂, R¹⁶ is —C(O)R¹⁶ or —C(O)OR¹¹, R¹⁰ is a hydrogen atom, C₁-C₄alkyl or cyclopropyl, R¹¹ is C₁-C₄ alkyl or C₁-C₄ haloalkyl, R¹⁷ isC₁-C₄ alkyl, R³² is a hydrogen atom or methyl, R³³ is C₁-C₄ alkyl orC₁-C₄ haloalkyl, p is an integer of from 0 to 2, and r is an integer offrom 0 to 2].

R¹-X: (C₁-C₄)alkyl optionally substituted with R¹⁸ [wherein R¹⁸ is ahalogen atom, phenyl substituted with (Z)_(m), D-2, D-4, D-6, D-8, D-9,D-12, D-14, D-15 or D-17, R¹⁵ is methyl, Z is a halogen atom, methyl,ethyl, trifluoromethyl, difluoromethoxy, methylthio, methylsulfinyl,methylsulfonyl, trifluoromethylsulfinyl or trifluoromethylsulfony, whenm and n are 2, the respective Z's may be identical with or differentfrom each other, m is an integer of 1 or 2, and n is an integer of from0 to 2].

Among them, as the scope of the substituent represented by R¹, morepreferred are R¹-I to R¹-IV, particularly preferred are R¹-I and R¹-II.

As the preferred range of the substituent represented by R² in thecompounds which fall within the present invention, the following setsmay, for example, be mentioned.

R²-I: A hydrogen atom.

R²-II: Methyl

R²-III Ethyl.

R²-IV: C₃-C₄ alkyl and phenyl.

R²-V: Fluoromethyl and trifluoromethyl.

R²-VI: Methoxymethyl, methylthiomethyl, methylsulfinylmethyl andmethylsulfonylmethyl.

R²-VII: Cyclopropyl and cyclobutyl.

Among them, as the scope of the substituted represented by R², morepreferred are R²-I to R²-III and R²-V, particularly preferred are R²-Iand R²-II.

As the scope of the substituent represented by R³ in the compounds whichfall within the present invention, the following sets may, for example,be mentioned.

R³-1: A hydrogen atom.

R³-II: Methyl.

R³-III: R³ forms a cyclopropyl ring together with R².

R³-IV: R³ forms, together with R², a C₃-C₅ alkylene chain to form a 4-to 6-membered ring together with the carbon atom attached to R² and R³.

R³-V: C₂-C₄ alkyl.

R³-VI: R³ form, together with R², a C₂-C₅ alkylene chain to form a 3- to6-membered ring together with the carbon atom attached to R² and R³,wherein the alkylene chain contains an oxygen atom or sulfur atom.

Among them, as the scope of the substituent represented by R³, morepreferred are R³-I to R³-III, and particularly preferred is R³-I.

As the scope of the substituent represented by R⁴ in the compounds whichfall within the present invention, the following sets may, for example,be mentioned.

R⁴-I: A hydrogen atom.

R⁴-II: C₁-C₄ alkylcarbonyl.

R⁴-III: C₁-C₄ alkoxycarbonyl.

R⁴-IV: C₁-C₄ haloalkylthio.

R⁴-V: C₁-C₄ alkyl, (C₁-C₂)alkyl substituted with R¹⁹ [wherein R¹⁹ iscyano or C₁-C₄ alkoxy], cyclopropyl, allyl and propargyl.

R⁴-VI: C₃-C₆ cycloalkyl, C₂-C₄ alkenyl and C₂-C₄ alkynyl.

R⁴-VII: (C₁-C₂)alkyl substituted with R¹⁹ [wherein R¹⁹ is −OR³⁶,—C(O)NH₂ or —C(S)NH₂, R³⁶ is C₂-C₄ haloalkyl, C₁-C₄ alkylcarbonyl, C₃-C₆cycloalkylcarbonyl or C₁-C₄ alkoxycarbonyl].

R⁴-VIII: —C(O)R²⁰ [wherein R²⁰ is C₁-C₄ alkoxymethyl, C₁-C₄alkylthiomethyl, C₁-C₄ alkylsulfonylmethyl, C₃-C₄ cycloalkyl or C₂-C₄alkenyl].

R⁴—IX: —C(O)OR²¹ [wherein R²¹ is C₁-C₄ haloalkyl, C₁-C₄alkoxy(C₁-C₂)alkyl, allyl or propargyl].

R⁴—X: C₁-C₄ alkoxy.

Among them, as the scope of the substituent represented by R⁴, morepreferred are R⁴-I to R⁴-IV, particularly preferred is R⁴-I.

The sets indicating the preferred range of each substituent in thecompounds which fall within the present invention may be combinedarbitrarily to indicate the preferred range of the compounds of thepresent invention.

The preferred range of G¹, G², R¹ and R² of the compound represented bythe formula (I) may be combined, for example, as shown in Table 1. Thecombinations shown in Table 1 merely exemplify the present invention,and the compound of the present invention represented by the formula (I)is by no means restricted thereto.

TABLE 1 G¹ R² G² R¹ G¹-I R²-I G²-I R¹-I G¹-I R²-II G²-I R¹-I G¹-I R²-IIIG²-I R¹-I G¹-I R²-V G²-I R¹-I G¹-I R²-VI G²-I R¹-I G¹-I R²-VII G²-I R¹-IG¹-I R²-II G²-I R¹-II G¹-I R²-V G²-I R¹-II G¹-I R²-II G²-I R¹-III G¹-IR²-II G²-I R¹-V G¹-I R²-I G²-II R¹-I G¹-I R²-II G²-II R¹-I G¹-I R²-IIIG²-II R¹-I G¹-I R²-IV G²-II R¹-I G¹-I R²-V G²-II R¹-I G¹-I R²-VI G²-IIR¹-I G¹-I R²-VII G²-II R¹-I G¹-I R²-I G²-II R¹-II G¹-I R²-II G²-II R¹-IIG¹-I R²-V G²-II R¹-II G¹-I R²-I G²-II R¹-III G¹-I R²-I G²-II R¹-IV G¹-IR²-I G²-II R¹-V G¹-I R²-I G²-II R¹-VI G¹-I R²-II G²-II R¹-VI G¹-I R²-IG²-II R¹-VII G¹-I R²-I G²-II R¹-VIII G¹-I R²-II G²-II R¹-VIII G¹-I R²-IG²-II R¹-IX G¹-I R²-I G²-II R¹-X G¹-I R²-II G²-III R¹-I G¹-I R²-IIG²-III R¹-II G¹-I R²-II G²-IV R¹-I G¹-I R²-II G²-IV R¹-II G¹-I R²-IIG²-V R¹-I G¹-I R²-II G²-V R¹-II G¹-I R²-I G²-VI R¹-I G¹-I R²-II G²-VIR¹-I G¹-I R²-I G²-VI R¹-II G¹-I R²-II G²-VI R¹-II G¹-I R²-I G²-VII R¹-IG¹-I R²-I G²-VII R¹-II G¹-I R²-I G²-VIII R¹-I G¹-I R²-II G²-VIII R¹-IG¹-I R²-I G²-VIII R¹-II G¹-I R²-II G²-VIII R¹-II G¹-I R²-I G²-IX R¹-IG¹-I R²-II G²-IX R¹-I G¹-I R²-I G²-IX R¹-II G¹-I R²-II G²-IX R¹-II G¹-IR²-II G²-X R¹-I G¹-I R²-II G²-X R¹-II G¹-I R²-II G²-XI R¹-I G¹-I R²-IIG²-XI R¹-II G¹-I R²-II G²-XII R¹-I G¹-I R²-II G²-XII R¹-II G¹-I R²-IIG²-XIII R¹-I G¹-I R²-I G²-XIV R¹-I G¹-I R²-I G²-XV R¹-I G¹-I R²-II G²-XVR¹-I G¹-I R²-I G²-XV R¹-II G¹-I R²-II G²-XVI R¹-I G¹-I R²-II G²-XVIIR¹-I G¹-I R²-I G²-XVIII R¹-I G¹-I R²-II G²-XIX R¹-I G¹-I R²-II G²-XXR¹-I G¹-I R²-II G²-XXI R¹-I G¹-I R²-II G²-XXII R¹-I G¹-I R²-II G²-XXIIIR¹-I G¹-I R²-I G²-XXIV R¹-I G¹-I R²-I G²-XXV R¹-I G¹-I R²-I G²-XXVI R¹-IG¹-I R²-II G²-XXVI R¹-I G¹-I R²-I G²-XXVI R¹-II G¹-I R²-II G²-XXVI R¹-IIG¹-I R²-I G²-XXVII R¹-I G¹-I R²-II G²-XXVII R¹-I G¹-I R²-I G²-XXVIIIR¹-I G¹-I R²-II G²-XXVIII R¹-I G¹-I R²-I G²-XXIX R¹-I G¹-I R²-II G²-XXIXR¹-I G¹-I R²-I G²-XXIX R¹-II G¹-I R²-II G²-XXIX R¹-II G¹-I R²-I G²-XXXR¹-I G¹-I R²-II G²-XXX R¹-I G¹-I R²-I G²-XXX R¹-II G¹-I R²-II G²-XXXR¹-II G¹-I R²-I G²-XXXI R¹-I G¹-I R²-I G²-XXXII R¹-I G¹-I R²-II G²-XXXIIR¹-I G¹-I R²-I G²-XXXIII R¹-I G¹-I R²-II G²-XXXIII R¹-I G¹-I R²-IG²-XXXIV R¹-I G¹-I R²-II G²-XXXIV R¹-I G¹-I R²-I G²-XXXV R¹-I G¹-I R²-IG²-XXXVI R¹-I G¹-II R²-I G²-II R¹-I G¹-II R²-II G²-II R¹-I G¹-II R²-IG²-II R¹-II G¹-II R²-II G²-II R¹-II G¹-II R²-I G²-XXVI R¹-I G¹-III R²-IIG²-I R¹-I G¹-III R²-II G²-I R¹-II G¹-III R²-I G²-II R¹-I G¹-III R²-IIG²-II R¹-I G¹-III R²-I G²-II R¹-II G¹-III R²-II G²-II R¹-II G¹-III R²-IG²-VI R¹-I G¹-III R²-I G²-VI R¹-II G¹-III R²-II G²-IX R¹-I G¹-III R²-IIG²-IX R¹-II G¹-III R²-II G²-XX R¹-I G¹-III R²-I G²-XXVI R¹-I G¹-IV R²-IG²-I R¹-I G¹-IV R²-II G²-I R¹-I G¹-IV R²-II G²-I R¹-II G¹-IV R²-I G²-IIR¹-I G¹-IV R²-II G²-II R¹-I G¹-IV R²-I G²-II R¹-II G¹-IV R²-II G²-IIR¹-II G¹-IV R²-I G²-VI R¹-I G¹-IV R²-I G²-VI R¹-II G¹-IV R²-II G²-IXR¹-I G¹-IV R²-II G²-IX R¹-II G¹-IV R²-II G²-XX R¹-I G¹-IV R²-I G²-XXVIR¹-I G¹-V R²-II G²-I R¹-I G¹-V R²-II G²-I R¹-II G¹-V R²-I G²-II R¹-IG¹-V R²-II G²-II R¹-I G¹-V R²-I G²-II R¹-II G¹-V R²-II G²-II R¹-II G¹-VR²-I G²-VI R¹-I G¹-V R²-I G²-VI R¹-II G¹-V R²-II G²-IX R¹-I G¹-V R²-IIG²-IX R¹-II G¹-V R²-II G²-XX R¹-I G¹-V R²-I G²-XXVI R¹-I G¹-VI R²-I G²-IR¹-I G¹-VI R²-II G²-I R¹-I G¹-VI R²-II G²-I R¹-II G¹-VI R²-I G²-II R¹-IG¹-VI R²-II G²-II R¹-I G¹-VI R²-I G²-II R¹-II G¹-VI R²-II G²-II R¹-IIG¹-VI R²-II G²-III R¹-I G¹-VI R²-II G²-III R¹-II G¹-VI R²-I G²-VI R¹-IG¹-VI R²-I G²-VI R¹-II G¹-VI R²-II G²-IX R¹-I G¹-VI R²-II G²-IX R¹-IIG¹-VI R²-I G²-XXVI R¹-I G¹-VII R²-II G²-I R¹-I G¹-VII R²-II G²-I R¹-IIG¹-VII R²-I G²-II R¹-I G¹-VII R²-II G²-II R¹-I G¹-VII R²-I G²-II R¹-IIG¹-VII R²-II G²-II R¹-II G¹-VII R²-I G²-VI R¹-I G¹-VII R²-I G²-VI R¹-IIG¹-VII R²-II G²-IX R¹-I G¹-VII R²-II G²-IX R¹-II G¹-VII R²-I G²-XXVIR¹-I G¹-VIII R²-II G²-I R¹-I G¹-VIII R²-II G²-I R¹-II G¹-VIII R²-I G²-IIR¹-I G¹-VIII R²-II G²-II R¹-I G¹-VIII R²-I G²-II R¹-II G¹-VIII R²-IIG²-II R¹-II G¹-VIII R²-I G²-VI R¹-I G¹-VIII R²-I G²-VI R¹-II G¹-VIIIR²-II G²-IX R¹-I G¹-VIII R²-II G²-IX R¹-II G¹-VIII R²-II G²-XX R¹-IG¹-VIII R²-I G²-XXVI R¹-I G¹-IX R²-I G²-I R¹-I G¹-IX R²-II G²-I R¹-IG¹-IX R²-II G²-I R¹-II G¹-IX R²-I G²-II R¹-I G¹-IX R²-II G²-II R¹-IG¹-IX R²-I G²-II R¹-II G¹-IX R²-II G²-II R¹-II G¹-IX R²-I G²-VI R¹-IG¹-IX R²-I G²-VI R¹-II G¹-IX R²-II G²-IX R¹-I G¹-IX R²-II G²-IX R¹-IIG¹-IX R²-II G²-XX R¹-I G¹-IX R²-I G²-XXVI R¹-I G¹-X R²-II G²-I R¹-I G¹-XR²-II G²-I R¹-II G¹-X R²-I G²-II R¹-I G¹-X R²-II G²-II R¹-I G¹-X R²-IG²-II R¹-II G¹-X R²-II G²-II R¹-II G¹-X R²-I G²-VI R¹-I G¹-X R²-I G²-VIR¹-II G¹-X R²-II G²-IX R¹-I G¹-X R²-II G²-IX R¹-II G¹-X R²-II G²-XX R¹-IG¹-X R²-I G²-XXVI R¹-I G¹-XI R²-I G²-II R¹-I G¹-XI R²-I G²-II R¹-IIG¹-XII R²-I G²-II R¹-I G¹-XIII R²-II G²-I R¹-I G¹-XIII R²-I G²-II R¹-IG¹-XIII R²-II G²-II R¹-I G¹-XIV R²-I G²-II R¹-I G¹-XV R²-I G²-II R¹-IG¹-XVI R²-II G²-I R¹-I G¹-XVI R²-I G²-II R¹-I G¹-XVII R²-I G²-II R¹-IG¹-XVIII R²-I G²-II R¹-I G¹-XVIII R²-II G²-III R¹-I G¹-XVIII R²-IIG²-III R¹-II G¹-XIX R²-I G²-II R¹-I G¹-XX R²-I G²-II R¹-I G¹-XXI R²-IG²-II R¹-I G¹-XXII R²-I G²-II R¹-I G¹-XXIII R²-II G²-I R¹-I G¹-XXIIIR²-II G²-I R¹-II G¹-XXIII R²-I G²-II R¹-I G¹-XXIII R²-II G²-II R¹-IG¹-XXIII R²-I G²-II R¹-II G¹-XXIII R²-II G²-II R¹-II G¹-XXIV R²-I G²-IIR¹-I G¹-XXV R²-II G²-II R¹-I G¹-XXVI R²-I G²-II R¹-I G¹-XXVII R²-II G²-IR¹-I G¹-XXVII R²-I G²-II R¹-I G¹-XXVIII R²-I G²-II R¹-I G¹-XXIX R²-IIG²-I R¹-I G¹-XXIX R²-II G²-I R¹-II G¹-XXIX R²-I G²-II R¹-I G¹-XXIX R²-IIG²-II R¹-I G¹-XXIX R²-I G²-II R¹-II G¹-XXIX R²-II G²-II R¹-II G¹-XXIXR²-I G²-VI R¹-I G¹-XXIX R²-I G²-VI R¹-II G¹-XXIX R²-II G²-IX R¹-IG¹-XXIX R²-II G²-IX R¹-II G¹-XXX R²-II G²-I R¹-I G¹-XXX R²-II G²-I R¹-IIG¹-XXX R²-I G²-II R¹-I G¹-XXX R²-II G²-II R¹-I G¹-XXX R²-I G²-II R¹-IIG¹-XXX R²-II G²-II R¹-II G¹-XXXI R²-I G²-II R¹-I G¹-XXXII R²-II G²-IR¹-I G¹-XXXII R²-II G²-I R¹-II G¹-XXXII R²-I G²-II R¹-I G¹-XXXII R²-IIG²-II R¹-I G¹-XXXII R²-I G²-II R¹-II G¹-XXXII R²-II G²-II R¹-IIG¹-XXXIII R²-II G²-I R¹-I G¹-XXXIII R²-II G²-I R¹-II G¹-XXXIII R²-IG²-II R¹-I G¹-XXXIII R²-II G²-II R¹-I G¹-XXXIII R²-I G²-II R¹-IIG¹-XXXIII R²-II G²-II R¹-II G¹-XXXIV R²-II G²-I R¹-I G¹-XXXIV R²-II G²-IR¹-II G¹-XXXIV R²-I G²-II R¹-I G¹-XXXIV R²-II G²-II R¹-I G¹-XXXIV R²-IG²-II R¹-II G¹-XXXIV R²-II G²-II R¹-II G¹-XXXV R²-II G²-I R¹-I G¹-XXXVR²-II G²-I R¹-II G¹-XXXV R²-I G²-II R¹-I G¹-XXXV R²-II G²-II R¹-IG¹-XXXV R²-I G²-II R¹-II G¹-XXXV R²-II G²-II R¹-II G¹-XXXVI R²-II G²-IR¹-I G¹-XXXVI R²-II G²-I R¹-II G¹-XXXVI R²-I G²-II R¹-I G¹-XXXVI R²-IIG²-II R¹-I G¹-XXXVI R²-I G²-II R¹-II G¹-XXXVI R²-II G²-II R¹-IIG¹-XXXVII R²-II G²-I R¹-I G¹-XXXVII R²-II G²-I R¹-II G¹-XXXVII R²-IG²-II R¹-I G¹-XXXVII R²-II G²-II R¹-I G¹-XXXVII R²-I G²-II R¹-IIG¹-XXXVII R²-II G²-II R¹-II G¹-XXXVIII R²-I G²-II R¹-I G¹-XXXIX R²-IG²-II R¹-I G¹-XL R²-I G²-II R¹-I G¹-XLI R²-II G²-I R¹-I G¹-XLI R²-IG²-II R¹-I G¹-XLII R²-II G²-I R¹-I G¹-XLII R²-II G²-I R¹-II G¹-XLII R²-IG²-II R¹-I G¹-XLII R²-II G²-II R¹-I G¹-XLII R²-I G²-II R¹-II G¹-XLIIR²-II G²-II R¹-II G¹-XLIII R²-II G²-I R¹-I G¹-XLIII R²-I G²-II R¹-IG¹-XLIII R²-II G²-II R¹-I G¹-XLIV R²-I G²-II R¹-I G¹-XLV R²-I G²-II R¹-IG¹-XLVI R²-I G²-II R¹-I

Some of the compounds of the present invention represented by theformula (I) can be converted, by ordinary methods, to acid additionsalts with hydrogen halides such as hydrofluoric acid, hydrochloricacid, hydrobromic acid and hydroiodic acid, with inorganic acids such asnitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloricacid, with sulfonic acids such as methanesulfonic acid, ethanesulfonicacid, trifluoromethanesulfonic acid, benzenesulfonic acid andp-toluenesulfonic acid, with carboxylic acids such as formic acid,acetic acid, propionic acid, trifluoroacetic acid, fumaric acid,tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid,benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acidand citric acid, with amino acids such as glutamic acid and asparticacid.

Some of the compounds of the present invention represented by theformula (I) can be converted, by ordinary methods, to metal salts withalkali metals such as lithium, sodium and potassium, with alkaline earthmetals such as calcium, barium and magnesium, with metals such asaluminum.

The pesticides herein mean fungicides and parasiticides for controllingharmful pathogens and parasites which infect/parasitize plants oranimals.

Plants herein mean grain, fruits and vegetables, cultivated as food forhuman, feed crop for livestock and poultry, ornamental plants of whichappearances are enjoyed, or Tracheophyta such as planting of parks,streets and the like, and specifically, the following plants may, forexample, be mentioned, but the present invention is not restrictedthereto.

Plants of the order Pinales belonging to the family Pinaceae such asJapanese Red Pine (Pinus densiflora), Scots Pine (Pinus sylvestris),Japanese Black Pine (Pinus thunbergii), etc.

Plants of the group Magnoliids belonging to the family Piperaceae suchas pepper (Piper nigrum), etc., the family Lauraceae such as Avocado(Persea americana), etc.

Plants of the group monocots belonging to the family Araceae such asKonjac (Amorphophallus koniac), Eddoe (Colocasia esculenta), etc., thefamily Dioscoreaceae such as Chinese yam (Dioscorea batatas), Japaneseyam (Dioscorea japonica), etc., the family Alliaceae such as Leek(Allium ampeloprasum var. porrum), Onion (Allium cepa), Rakkyo (Alliumchinense), Welsh onion (Allium fistulosum), Garlic (Allium sativum),Chives (Allium schoenoprasum), Chive (Allium schoenoprasum var.foliosum), Oriental garlic (Allium tuberosum), Scallion (Allium xwakegi), etc., the family Asparagaceae such as Asparagus (Asparagusofficinalis), etc., the family Arecaceae subfamily Arecoideae such asCoconut palm (Cocos nucifera), Oil palm (Elaeis quineensis), etc., thefamily Arecaceae the subfamily Coryphoideae such as Date palm (Phoenixdactylifera), etc., the family Bromeliaceae such as Pineapple (Ananascomosus), etc., the family Poaceae subfamily Ehrhartoideae such as Rice(Oryza sativa), etc., the family Poaceae subfamily Pooideae such as Bentgrass (Agrostis spp.), Blue grass (Poa spp.), Barley (Hordeum vulgare),Wheat (Triticum aestivum, T. durum), Rye (Secale cereale), etc., thefamily Poaceae subfamily Chloridoideae such as Bermuda grass (Cynodondactylon), Grass (Zoysia spp.), etc., the family Poaceae subfamilyPanicoideae such as Sugarcane (Saccharum officinarum), Sorgum (Sorghumbicolor), Corn (Zea mays), etc., the family Musaceae such as Banana(Musa spp.), etc., the family Zingiberaceae such as Myoga (Zingibermioga), Ginger (Zingiber officinale), etc.

Plants of the group eudicots belonging to the family Nelumbonaceae suchas Lotus root (Nelumbo nucifera), etc., the family Fabaceae such asPeanut (Arachis hypogaea), Chickpea (Cicer arietinum), Lentil (Lensculinaris), Pea (Pisum sativum), Broad bean (Vicia faba), Soybean(Glycine max), Common bean (Phaseolus vulgaris), Adzuki bean (Vignaangularis), Cowpea (Vigna unquiculata), etc., the family Cannabaceaesuch as Hop (Humulus lupulus), etc., the family Moraceae such as FigTree (Ficus carica), Mulberry (Morus spp.), etc., the family Rhamnaceaesuch as Common jujube (Ziziphus jujuba), etc., the family Rosaceaesubfamily Rosoideae such as Strawberry (Fragaria), Rose (Rosa spp.),etc., the family Rosaceae subfamily Maloideae such as Japanese loquat(Eriobotrya japonica), Apple (Malus pumila), European Pear (Pyruscommunis), Nashi Pear (Pyrus pyrifolia var. culta), etc., the familyRosaceae subfamily Prunoideae such as Peach (Amygdalus persica), Apricot(Prunus armeniaca), Cherry (Prunus avium), Prune (Prunus domestica),Almond (Prunus dulcis), Japanese Apricot (Prunus mume), Japanese Plum(Prunus salicina), Cerasus speciosa, Cerasus x yedoensis‘Somei-yoshino’, etc., the family Cucurbitaceae such as Winter melon(Benincasa hispida), Watermelon (Citrullus lanatus), Bottle gourd(Lagenaria siceraria var. hispida), Luffa (Luffa cylindrica), Pumpkin(Cucurbita spp.), Zucchini (Cucurbita pepo), Bitter melon (Momordicacharantia var. pavel), Muskmelon (Cucumis melo), Oriental pickling melon(Cucumis melo var. conomon), Oriental melon (Cucumis melo var. makuwa),Cucumber (Cucumis sativus), etc., the family Fagaceae such as JapaneseChestnut (Castanea crenata), etc., the family Juglandaceae such asWalnut (Juqlans spp.), etc., the family Anacardiaceae such as Cashew(Anacardium occidentale), Mango (Mangifera indica), Pistachio (Pistaciavera), etc., the family Rutaceae subfamily Rutoideae such as Japanesepepper (Zanthoxylum piperitum), etc., the family Rutaceae subfamilyAurantioideae such as Bitter orange (Citrus aurantium), Lime (Citrusaurantifolia), Hassaku orange (Citrus hassaku), Yuzu (Citrus junos),Lemon (Citrus limon), Natsumikan (Citrus natsudaidai), Grapefruit(Citrus x paradisi), Orange (Citrus sinensis), Kabosu (Citrussphaerocarpa), Sudachi (Citrus sudachi), Mandarin Orange (Citrustanqerina), Satsuma (Citrus unshiu), Kumquat (Fortunella spp.), etc.,

the family Brassicaceae such as Horseradish (Armoracia rusticana),Mustard (Brassica juncea), Takana (Brassica juncea var. inteqrifolia),Rapeseed (Brassica napus), Cauliflower (Brassica oleracea var.botrytis), Cabbage (Brassica oleracea var. capitata), Brussels sprout(Brassica oleracea var. gemmifera), Broccoli (Brassica oleracea var.italica), Green pak choi (Brassica raga var. chinensis), Nozawana(Brassica raga var. hakabura), Napa cabbage (Brassica rapa var.nippo-oleifera), Potherb Mustard (Brassica raga var. nipposinica), Napacabbage (Brassica rapa var. pekinensis), Turnip leaf (Brassica raga var.perviridis), Turnip (Brassica rapa var. rapa), Garden rocket (Erucavesicaria), Daikon (Raphanus sativus var. longipinnatus), Wasabi(Wasabia japonica), etc., the family Caricaceae such as Papaya (Caricapapaya), etc., the family Malvaceae such as Okra (Abelmoschusesculentus), Cotton plant (Gossypium spp.), Cacao (Theobroma cacao),etc., the family Vitaceae such as Grape (Vitis spp.), etc., the familyAmaranthaceae such as Sugar beet (Beta vulgaris ssp. vulgaris var.altissima), Table beet (Beta vulgaris ssp. vulgaris var. vulgaris),Spinach (Spinacia oleracea), etc., the family Polygonaceae such asBuckwheat (Fagopyrum esculentum), etc., the family Ebenaceae such asKaki Persimmon (Diospyros kaki), etc., the family Theaceae scuh as Teaplant (Camellia sinensis), etc., the family Actinidiaceae such asKiwifruit (Actinidia deliciosa, A. chinensis), etc., the familyEricaceae such as Blueberry (Vaccinium spp.), Cranberry (Vacciniumspp.), etc., the family Rubiaceae such as Coffee plants (Coffea spp.),etc., the family Lamiaceae such as Lemon balm (Melissa officinalis),Mint (Mentha spp.), Basil (Ocimum basilicum), Shiso (Perilla frutescensvar. crispa), Perilla frutescens var. frutescens, Common Sage (Salviaofficinalis), Thyme (Thymus spp.), etc., the family Pedaliaceae such asSesame (Sesamum indicum), etc., the family Oleaceae such as Olive (Oleaeuropaea), etc. the family Convolvulaceae such as Sweet potato (Ipomoeabatatas), etc., the family Solanaceae such as Tomato (Solanumlycopersicum), Eggplant (Solanum melongena), Potato (Solanum tuberosum),Chili pepper (Capsicum annuum), Bell pepper (Capsicum annuum var.‘grossum’), Tobacco (Nicotiana tabacum), etc., the family Apiaceae suchas Celery (Apium graveolens var. dulce), Coriander (Coriandrum sativum),Japanese honeywort (Cryptotaenia Canadensis subsp. japonica), Carrot(Daucus carota subsp. sativus), Parsley (Petroselium crispum), Italianparsley (Petroselinum neapolitanum), etc., the family Araliaceae such asUdo (Aralia cordata), Aralia elata, etc., the family Asteraceaesubfamily Carduoideae such as Artichoke (Cynara scolymus), etc., thefamily Asteraceae subfamily Asteraceae such as Chicory (Cichoriumintybus), Lettuce (Lactuca sativa), etc., the family Asteraceaesubfamily Asteraceae such as Florists' daisy (Dendranthemagrandiflorum), Crown daisy (Glebionis coronaria), Sunflower (Helianthusannuus), Fuki (Petasites japonicus), Burdock (Arctium lappa), etc.

Animals herein mean human, companion creatures/pets, livestock/poultry,and vertebrate such as research/laboratory animals, and specifically,the following animals may, for example, be mentioned, but the presentinvention is not restricted thereto.

Animals of the class Mammalia belonging to the family Cebidae such asTufted capuchin (Cebus apella), etc., the family Cercopithecidae such asCrab-eating macaque (Macaca fascicularis), Rhesus macaque (Macacamulatta), etc., the family Homimidae such as Chimpanzee (Pantroglodytes), Human (Homo sapiens), etc., the family Leporidae such asEuropean rabbit (Oryctolaqus cuniculus), etc., the family Chinchillidaesuch as Long-tailed chinchilla (Chinchilla lanigera), etc., the familyCaviidae such as Guinea pig (Cavia porcellus), etc., the familyCricetidae such as Golden hamster (Mesocricetus auratus), Djungarianhamster (Phodopus sunqorus), Chinese hamster (Cricetulus griseus), etc.,the family Muridae such as Mongolian gerbil (Meriones unguiculatus),House mouse (Mus musculus), Black rat (Rattus rattus), etc., the familySciuridae such as Chipmunk (Tamias sibiricus), etc., the familyCamelidae such as Dromedary (Camelus dromedarius), Bactrian camel(Camelus bactrianus), Alpaca (Vicuqna pacos), Llama (Lama glama), etc.,the family Suidae such as Pig (Sus scrofa domesticus), etc., the familyCervidae such as Reindeer (Ranqifer tarandus), Red deer (Cervuselaphus), etc., the family Bovidae such as Yak (Bos grunniens), Cattle(Bos taurus), Water buffalo (Bubalus arnee), Goat (Capra hircus), Sheep(Ovis aries), etc., the family Felidae such as Cat (Felis silvestriscatus), etc., the family Canidae such as Dog (Canis lupus familiaris),Red fox (Vulpes vulpes), etc., the family Mustelidae such as Europeanmink (Mustela lutreola), American mink (Mustela vison), Ferret (Mustelaputorius furo), etc., the family Equidae such as Donkey (Equus asinus),Horse (Equus caballus), etc., the family Macropodidae such as Redkangaroo (Macropus rufus), etc.

Animals of the class Ayes belonging to the family Struthionidae such asOstrich (Struthio camelus), etc., the family Rheidae such as Americanrhea (Rhea americana), etc., the family Dromaiidae such as Emu (Dromaiusnovaehollandiae), etc., the family Phasianidae such as Ptarmigan(Laqopus muta), Wild turkey (Meleagris gallopavo), Japanese quail(Coturnix japonica), Chicken (Gallus gallus domesticus), Common pheasant(Phasianus colchicus), Golden pheasant (Chrysolophus pictus), Indianpeafowl (Pavo cristatus), etc., the family Numididae such as Helmetedguineafowl (Numida meleagris), etc., the family Anatidae such as Mallard(Anas platyrhynchos), Domesticated duck (Anas platyrhynchos var.domesticus), Spot-billed duck (Anas poecilorhyncha), Greylag goose(Anser anser), Swan goose (Anser cygnoides), Whooper swan (Cygnuscygnus), Mute swan (Cygnus olor), etc., the family Columbidae such asRock dove (Columba livia), Oriental turtle dove (Streptopeliaorientalis), European turtle dove (Streptopelia turtur), etc., thefamily Cacatuidae such as Sulphur-crested cockatoo (Cacatua galerita),Galah (Eolophus roseicapilla), Cockatiel (Nymphicus hollandicus), etc.,the family Psittacidae such as Rosy-faced lovebird (Agapornisroseicollis), Blue-and-yellow macaw (Ara ararauna), Scarlet Macaw (Aramacao), Budgerigar (Melopsittacus undulatus), African grey parrot(Psittacus erithacus), etc., the family Sturnidae such as Common hillmyna (Gracula religiosa), etc., the family Estrildidae such as Redavadavat (Amandava amandava), Zebra finch (Taeniopygia guttata),Bengalese finch (Lonchura striata var. domestica), Java sparrow (Paddaoryzivora), etc., the family Fringillidae such as Domestic canary(Serinus canaria domestica), European goldfinch (Carduelis carduelis),etc.

Animals of the class Reptilia belonging to the family Chamaeleonidaesuch as Veiled chameleon (Chamaeleo calyptratus), etc., the familyIguanidae such as Green iguana (Iguana iguana), Carolina anole (Anoliscarolinensis), etc., the family Varanidae such as Nile monitor (Varanusniloticus), Water monitor (Varanus salvator), etc., the family Scincidaesuch as Solomon islands skink (Corucia zebrata), etc., the familyColubridae such as Beauty rat snake (Elaphe taeniura), etc., the familyBoidae such as Boa constrictor (Boa constrictor), etc., the familyPythonidae such as Indian python (Python molurus), Reticulated python(Python reticulatus), etc., the family Chelydridae such as Commonsnapping turtle (Chelydra serpentina), etc., the family Emydidae such asDiamondback terrapin (Malaclemys terrapin), Pond slider (Trachemysscripta), etc., the family Geoemydidae such as Japanese pond turtle(Mauremys japonica), etc., the family Testudimidae such as Central Asiantortoise (Agrionemys horsfieldii), etc., the family Trionychidae such asSoft-shelled turtle (Pelodiscus sinensis), etc., the familyAlligatoridae such as American alligator (Alligator mississippiensis),Black caiman (Melanosuchus niger), etc., the family Crocodylidae such asSiamese crocodile (Crocodylus siamensis), etc.

Animals of the class Actinopterygii belonging to the family Cyprimidaesuch as Carp (Cyprinus carpio), Goldfish (Carassius auratus auratus),Zebrafish (Danio rerio), etc., the family Cobitidae such as Kuhli loach(Pangio kuhlii), etc., the family Characidae such as Red piranha(Pygocentrus nattereri), Neon tetra (Paracheirodon innesi), etc., thefamily Salmonidae such as Maraena whitefish (Coregonus lavaretusmaraena), Coho salmon (Oncorhynchus kisutsh), Rainbow trout(Oncorhynchus mykiss), Chinook salmon (Oncorhynchus tshawytscha),Atlantic salmon (Salmo salar), Brown trout (Salmo trutta), etc., thefamily Percichthyidae such as Spotted sea bass (Lateolabrax maculatus),etc., the family Serranidae such as Sea goldie (Pseudanthiassquamipinnis), Longtooth grouper (Epinephelus bruneus), Convict grouper(Epinephelus septemfasciatus), etc., the family Centrarchidae such asBluegill (Lepomis macrochirus), etc., the family Carangidae such asWhite trevally (Pseudocaranx dentex), Greater amberjack (Serioladumerili), Japanese amberjack (Seriola quinqueradiata), etc., the familySparidae such as Red sea bream (Pagrus major), etc., the familyCichlidae such as Nile tilapia (Oreochromis niloticus), Angelfish(Pterophyllum scalare), etc., the family Scombridae such as Pacificbluefin tuna (Thunnus orientalis), etc., the family Tetraodontidae suchas Japanese pufferfish (Takifugu rubripes), etc.

Pathogens herein mean microorganisms which cause plant diseases andanimal infections, and specifically, the following microorganisms may,for example, be mentioned, but the present invention is not restrictedthereto.

Fungi of the phylum Ascomycota, such as Taphrina spp. (e.g. Taphrinadeformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candidaspp.(e.g. Candida albicans, C. sorbosa, etc.), Pichia spp.(e.g. Pichiakluyveri, etc.), Geotrichum spp., Capnodium spp., Fumago spp.,Hypocapnodium spp., Cercospora spp.(e.g. Cercospora apii, C. asparagi,C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata,etc.), Cercosporidium spp., Cladosporium spp.(e.g. Cladosporiumcolocasiae, C. cucumerinum, C. variabile, etc.), Davidiella spp.,Didymosporium spp., Heterosporium spp. (e.g. Heterosporium allii, etc.),Mycosphaerella spp. (e.g. Mycosphaerella arachidis, M. berkeleyi, M.cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M.pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. (e.g.Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. (e.g.Paracercospora egenula, etc.), Phaeoisariopsis spp., Phaeoramulariaspp., Pseudocercospora spp. (e.g. Pseudocercospora abelmoschi, P.fuliqena, P. vitis, etc.), Pseudocercosporella spp. (e.g.Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramulariaspp., Septoqloeum spp., Septoria spp. (e.g. Septoria albopunctata, S.apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulinaspp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigminaspp., Elsinoe spp. (e.g. Elsinoe ampelina, E. araliae, E. fawcettii,etc.), Sphaceloma spp. (e.g. Sphaceloma caricae, etc.), Ascochyta spp.(e.g. Ascochyta pisi, etc.), Corynespora spp. (e.g. Corynesporacassiicola, etc.), Leptosphaeria spp. (e.g. Leptosphaeria coniothyrium,L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp.,Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternariaspp. (e.g. Alternaria alternata, A. brassicae, A. brassicicola, A.citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A.panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g.Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g. Cochliobolusheterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g.Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleosporaspp. (e.g. Pleospora herbarum, etc.), Pyrenophora spp. (e.g. Pyrenophoragraminea, P. teres, etc.), Setosphaeria spp. (e.g. Setosphaeria turcica,etc.), Stemphylium spp. (e.g. Stemphylium botryosum, S. lycopersici, S.solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (e.g.Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.),Didymella spp. (e.g. Didymella bryoniae, D. fabae, etc.), Hendersoniaspp., Phoma spp. (e.g. Phoma erratica var. mikan, P. exiqua var. exiqua,P. wasabiae, etc.), Pyrenochaeta spp. (e.g. Pyrenochaeta lycopersici,etc.), Stagonospora spp. (e.g. Stagonospora sacchari, etc.),Botryosphaeria spp. (e.g. Botryosphaeria berengeriana f. sp. piricola,B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp.,Lasiodiplodia spp. (e.g. Lasiodiplodia theobromae, etc.), Macrophomaspp., Macrophomina spp., Neofusicoccum spp., Phyllosticta spp. (e.g.Phyllosticta zingiberis, etc.), Schizothyrium spp. (e.g. Schizothyriumpomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp.,Penicillium spp. (e.g. Penicillium digitatum, P. italicum, P.sclerotigenum, etc.), Microsporum spp., Trichophyton spp. (e.g.Trichophyton mentagrophytes, T. rubrum, etc.), Histoplasma spp.,Blumeria spp. (e.g. Blumeria graminis f. sp. hordei, B. g. f. sp.tritici, etc.), Erysiphe spp. (e.g. Erysiphe betae, E. cichoracearum, E.c. var. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp.(e.g. Golovinomyces cichoracearum var. latisporus, etc.), Leveillulaspp. (e.g. Leveillula taurica, etc.), Microsphaera spp., Oidium spp.(e.g. Oidium neolycopersici, etc.), Phyllactinia spp. (e.g. Phyllactiniakakicola, P. mali, P. moricola, etc.), Podosphaera spp. (e.g.Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var.tridactyla, P. xanthii, etc.), Sphaerotheca spp. (e.g. Sphaerothecaaphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (e.g. Uncinulanecator, U. n. var. necator, etc.), Uncinuliella spp. (e.g. Uncinuliellasimulans var. simulans, U. s. var. tandae, etc.), Blumeriella spp. (e.g.Blumeriella jaapii, etc.), Cylindrosporium spp., Diplocarpon spp. (e.g.Diplocarpon mali, D. mespili, D. rosae, etc.), Gloeosporium spp. (e.g.Gloeosporium minus, etc.), Marssonina spp., Tapesia spp. (e.g. Tapesiaacuformis, T. yallundae, etc.), Lachnum spp., Scleromitrula spp.,Botryotinia spp. (e.g. Botryotinia fuckeliana, etc.), Botrytis spp.(e.g. Botrytis allii, B. byssoidea, B. cinerea, B. elliptica, B. fabae,B. squamosa, etc.), Ciborinia spp., Grovesinia spp., Monilia mumecola,Monilinia spp. (e.g. Monilinia fructicola, M. fructigena, M. laxa, M.mali, M. vaccinii-corymbosi, etc.), Sclerotinia spp. (e.g. Sclerotiniaborealis, S. homoeocarpa, S. minor, S. sclerotiorum, etc.), Valdensiaspp. (e.g. Valdensia heterodoxa, etc.), Claviceps spp. (e.g. Clavicepssorqhi, C. sorghicola, etc.), Epichloe spp., Ephelis japonica,Villosiclava virens, Hypomyces spp. (e.g. Hypomyces solani f. sp. mori,H. s. f. sp. pisi, etc.), Trichoderma spp. (e.g. Trichoderma viride,etc.), Calonectria spp. (e.g. Calonectria ilicicola, etc.), Candelosporaspp., Cylindrocarpon spp., Cylindrocladium spp., Fusarium spp. (e.g.Fusarium arthrosporioides, F. crookwellense, F. culmorum, F.cuneirostrum, F. oxysporum, F. o. f. sp. adzukicola, F. o. f. sp. allii,F. o. f. sp. asparaqi, F. o. f. sp. batatas, F. o. f. sp. cepae, F. o.f. sp. colocasiae, F. o. f. sp. conglutinans, F. o. f. sp. cubense, F.o. f. sp. cucumerinum, F. o. f. sp. fabae, F. o. f. sp. fragariae, F. o.f. sp. lactucae, F. o. f. sp. lagenariae, F. o. f. sp. lycopersici, F.o. f. sp. melongenae, F. o. f. sp. melonis, F. o. f. sp. nelumbinicola,F. o. f. sp. niveum, F. o. f. sp. radicis-lycopersici, F. o. f. sp.raphani, F. o. f. sp. spinaciae, F. sporotrichioides, F. solani, F. s.f. sp. cucurbitae, F. s. f. sp. eumartii, F. s. f. sp. pisi, F. s. f.sp. radicicola, etc.), Gibberella spp. (e.g. Gibberella avenacea, G.baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectriaspp., Ophionectria spp., Caldariomyces spp., Myrothecium spp.,Trichothecium spp., Verticillium spp. (e.g. Verticillium albo-atrum, V.dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g. Ceratocystisficicola, C. fimbriata, etc.), Thielaviopsis spp. (e.g. Thielaviopsisbasicola, etc.), Adisciso spp., Monochaetia spp., Pestalotia spp. (e.g.Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (e.g.Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.),Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp.(e.g. Rosellinia necatrix, etc.), Monoqraphella spp. (e.g. Monographellanivalis, etc.), Ophiostoma spp., Cryphonectria spp. (e.g. Cryphonectriaparasitica, etc.), Diaporthe spp. (e.g. Diaporthe citri, D. kyushuensis,D. nomurai, D. tanakae, etc.), Diaporthopsis spp., Phomopsis spp. (e.g.Phomopsis asparaqi, P. fukushii, P. obscurans, P. vexans, etc.),Cryptosporella spp., Discula spp. (e.g. Discula theae-sinensis, etc.),Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp., Melanconisspp., Cytospora spp., Leucostoma spp., Valsa spp. (e.g. Valsaceratosperma, etc.), Tubakia spp., Monosporascus spp., Clasterosporiumspp., Gaeumannomyces spp. (e.g. Gaeumannomyces graminis, etc.),Magnaporthe spp. (e.g. Magnaporthe grisea, etc.), Pyricularia spp. (e.g.Pyricularia zingiberis, etc.), Monilochaetes infuscans, Colletotrichumspp. (e.g. Colletotrichum acutatum, C. capsici, C. cereale, C.destructivum, C. fraqariae, C. lindemuthianum, C. niqrum, C. orbiculare,C. spinaciae, etc.), Glomerella spp. (e.g. Glomerella cinqulata, etc.),Khuskia oryzae, Phyllachora spp. (e.g. Phyllachora pomigena, etc.),Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g. Cephalosporiumgramineum, etc.), Epicoccum spp., Gloeocercospora sorghi,Mycocentrospora spp., Peltaster spp. (e.g. Peltaster fructicola, etc.),Phaeocytostroma spp., Phialophora spp. (e.g. Phialophora gregata, etc.),Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporiumspp. (e.g. Rhynchosporium secalis, etc.), Sarocladium spp., Coleophomaspp., Helicoceras oryzae, etc. Fungi of the phylum Basidiomycota, suchas Septobasidium spp. (e.g. Septobasidium boqoriense, S. tanakae, etc.),Helicobasidium spp. (e.g. Helicobasidium longisporum, etc.),Coleosporium spp. (e.g. Coleosporium plectranthi, etc.), Cronartiumspp., Phakopsora spp. (e.g. Phakopsora artemisiae, P. nishidana, P.pachyrhizi, etc.), Physopella spp. (e.g. Physopella ampelopsidis, etc.),Kuehneola spp. (e.g. Kuehneola japonica, etc.), Phragmidium spp. (e.g.Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, etc.),Gymnosporangium spp. (e.g. Gymnosporangium asiaticum, G. yamadae, etc.),Puccinia spp. (e.g. Puccinia allii, P. brachypodii var. poae-nemoralis,P. coronata, P. c. var. coronata, P. cynodontis, P. graminis, P. g.subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala,P. recondita, P. striiformis var. striiformis, P. tanaceti var.tanaceti, P. tokyensis, P. zoysiae, etc.), Uromyces spp. (e.g. Uromycesphaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var.viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucoteliumspp., Tranzschelia spp. (e.g. Tranzschelia discolor, etc.), Aecidiumspp., Blastospora spp. (e.g. Blastospora smilacis, etc.), Uredo spp.,Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g. Sporisoriumscitamineum, etc.), Ustilago spp. (e.g. Ustilago maydis, U. nuda, etc.),Entyloma spp., Exobasidium spp. (e.g. Exobasidium reticulatum, E.vexans, etc.), Microstroma spp., Tilletia spp. (e.g. Tilletia caries, T.controversa, T. laevis, etc.), Itersonilia spp. (e.g. Itersoniliaperplexans, etc.), Cryptococcus spp., Bovista spp. (e.g. Bovistadermoxantha, etc.), Lycoperdon spp. (e.g. Lycoperdon curtisii, L.perlatum, etc.), Conocybe spp. (e.g. Conocybe apala, etc.), Marasmiusspp. (e.g. Marasmius oreades, etc.), Armillaria spp., Helotium spp.,Lepista spp. (e.g. Lepista subnuda, etc.), Sclerotium spp. (e.g.Sclerotium cepivorum, etc.), Typhula spp. (e.g. Typhula incarnata, T.ishikariensis var. ishikariensis, etc.), Athelia spp. (e.g. Atheliarolfsii, etc.), Ceratobasidium spp. (e.g. Ceratobasidium cornigerum,etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g. Rhizoctonia solani,etc.), Thanatephorus spp. (e.g. Thanatephorus cucumeris, etc.),Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp.,Chondrostereum purpureum, Phanerochaete spp., etc.

Fungi of the phylum Chitridiomycota such as Olpidium spp., etc.

Fungi of the phylum Blastocladiomycota such as Physoderma spp., etc.

Fungi of the phylum Mucoromycotina such as Choanephora spp.,Choanephoroidea cucurbitae, Mucor spp. (e.g. Mucor fragilis, etc.),Rhizopus spp. (e.g. Rhizopus arrhizus, R. chinensis, R. oryzae, R.stolonifer var. stolonifer, etc.), etc.

Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g.Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp.subterranea, etc.

Microorganisms of the phylum Heterokontophyta class Oomycetes such asAphanomyces spp. (e.g. Aphanomyces cochlioides, A. raphani, etc.),Albugo spp. (e.g. Albugo macrospora, A. wasabiae, etc.), Bremia spp.(e.g. Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerosporaspp., Peronospora spp. (e.g. Peronospora alliariae-wasabi, P.chrysanthemi-coronaria, P. destructor, P. farinosa f. sp. spinaciae, P.manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g.Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonosporaspp. (e.g. Pseudoperonospora cubensis, etc.), Sclerophthora spp.,Phytophthora spp. (e.g. Phytophthora cactorum, P. capsici, P. citricola,P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis,P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignaef. sp. adzukicola, etc.), Pythium spp. (e.g. Pythium afertile, P.aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P.buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P.irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P.paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P.ultimum var. ultimum, P. vanterpoolii, P. vexans, P. volutum, etc.),etc.

Gram-positive bacteria of the phylum Actinobacteria such as Clavibacterspp. (e.g. Clavibacter michiganensis subsp. michiganensis, etc.),Curtobacterium spp., Leifsonia spp. (e.g. Leifsonia xyli subsp. xyli,etc.), Streptomyces spp. (e.g. Streptomyces ipomoeae, etc.), etc.

Gram-positive bacteria of the phylum Firmicutes such as Clostridium sp.,etc.

Gram-positive bacteria of the phylum Tenericutes such as Phytoplasma,etc.

Gram-negative bacteria of the phylum Proteobacteria such as Rhizobiumspp. (e.g. Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderiaspp. (e.g. Burkholderia andropogonis, B. cepacia, B. gladioli, B.glumae, B. plantarii, etc.), Acidovorax spp. (e.g. Acidovorax avenaesubsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillumspp., Ralstonia spp. (e.g. Ralstonia solanacearum, etc.), Xanthomonasspp. (e.g. Xanthomonas albilineans, X. arboricola pv. pruni, X.axonopodis pv. vitians, X. campestris pv. campestris, X. c. pv.cucurbitae, X. c. pv. glycines, X. c. pv. manqiferaeindicae, X. c. pv.nigromaculans, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzaepv. oryzae, etc.), Pseudomonas spp. (e.g. Pseudomonas cichorii, P.fluorescens, P. marginalis, P. m. pv. marginalis, P. savastanoi pv.glycinea, P. syrinqae, P. s. pv. actinidiae, P. s. pv. eriobotryae, P.s. pv. helianthi, P. s. pv. lachrymans, P. s. pv. maculicola, P. s. pv.mori, P. s. morsprunorum, P. s. pv. spinaciae, P. s. pv. syringae, P. s.pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. (e.g.Brenneria niqrifluens, etc.), Dickeya spp. (e.g. Dickeya dianthicola, D.zeae, etc.), Erwinia spp. (e.g. Erwinia amylovora, E. rhapontici, etc.),Pantoea spp., Pectobacterium spp. (e.g. Pectobacterium atrosepticum, P.carotovorum, P. wasabiae, etc.), etc.

As specific examples the plant diseases and animal infections caused byinfection/proliferation of such pathogens, the following plant diseasesand animal infections may, for example, be mentioned, but the presentinvention is not restricted thereto.

Plant Diseases:

Leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Leaf spot(Cercospora asparaqi), Cercospora leaf spot (Cercospora beticola),Frogeye leaf spot (Cercospora capsici), Angular leaf spot (Cercosporakaki), Purple stain (Cercospora kikuchii), Brown Leaf spot(Mycosphaerella arachidis), Cylindrosporium leaf spot (Mycosphaerellacerasella, Blumeriella jaapii), Speckled leaf blotch (Mycosphaerellapraminicola), Circular leaf spot (Mycosphaerella nawae), Mycosphaerellablight (Mycosphaerella pinodes), Leaf spot (Mycosphaerella zinqiberis),Leaf mold (Mycovellosiella fulva), Leaf mold (Mycovellosiellanattrassii), Cercospora leaf mold (Pseudocercospora fuligena),Isariopsis leaf spot (Pseudocercospora vitis), Leaf spot(Pseudocercosporella capsellae), Leaf spot (Septoria chrysanthemella),Leaf blight (Septoria obesa), Anthracnose (Elsinoe ampelina), Spotanthracnose (Elsinoe araliae), Scab (Elsinoe fawcettii), Leaf spot(Ascochyta pisi), Corynespora leaf spot (Corynespora cassiicola), Stemcanker (Leptosphaeria coniothyrium), Leaf spot (Alternaria alternata),Leaf blight (Alternaria dauci), Black spot (Alternaria kikuchiana),Alternaria blotch (Alternaria mali), Alternaria leaf spot (Alternariaporri), Target spot (Bipolaris sorghicola), Southern leaf blight(Cochliobolus heterostrophus), Brown spot (Cochliobolus miyabeanus), Tipblight (Pleospora herbarum), Stripe (Pyrenophora graminea), Net blotch(Pyrenophora teres), Leaf blight (Setosphaeria turcica), Northern leafblight (Setosphaeria turcica), Leaf spot (Stemphylium botryosum), Scab(Venturia carpophila), Scab (Venturia lnaequalis), Scab (Venturianashicola), Gummy stem blight (Didymella bryoniae), Leaf spot (Phomaexigua var. exigua), Streak (Phoma wasabiae), Ring rot (Botryosphaeriaberengeriana f. sp. piricola), Soft rot (Botryosphaeria dothidea,Lasiodiplodia theobromae, Diaporthe sp.), Common green mold (Penicilliumdigitatum), Blue mold (Penicillium italicum), Powdery mildew (Blumeriaqraminis f. sp. hordei), Powdery mildew (Blumeria qraminis f. sp.tritici), Powdery mildew (Erysiphe betae, Leveillula taurica, Oidiumsp., Podosphaera xanthii), Powdery mildew (Erysiphe cichoracearum,Leveillula taurica, Sphaerotheca fuliqinea), Powdery mildew (Erysipheheraclei), Powdery mildew (Erysiphe pisi), Powdery mildew (Leveillulataurica, Oidium neolycopersici, Oidium sp.), Powdery mildew (Leveillulataurica), Powdery mildew (Oidium sp., Podosphaera xanthii), Powderymildew (Oidium sp.), Powdery mildew (Phyllactinia kakicola), Powderymildew (Podosphaera fusca), Powdery mildew (Podosphaera leucotricha),Powdery mildew (Podosphaera pannosa, Uncinuliella simulans var.simulans, U. s. var. tandae), Powdery mildew (Podosphaera xanthii),Powdery mildew (Sphaerotheca aphanis var. aphanis), Powdery mildew(Sphaerotheca fuliginea), Powdery mildew (Uncinula necator, U. n. var.necator), Blotch (Diplocarpon mali), Black spot (Diplocarpon rosae),Gray mold neck rot (Botrytis allii), Gray mold, Botrytis blight(Botrytis cinerea), Leaf blight (Botrytis cinerea, B. byssoidea, B.squamosa), Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae),Brown rot (Monilinia fructicola, M. fructiqena, M. laxa), Blossom blight(Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Cottony rot,Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut(Villosiclava virens), Root necrosis (Calonectria ilicicola), Fusariumblight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G.zeae, Monographella nivalis), Fusarium blight (Fusarium culmorum,Gibberella avenacea, G. zeae), Dry rot (Fusarium oxysporum, F. solani f.sp. radicicola), Brown rot (Fusarium oxysporum, F. solani f. sp. pisi,F. s. f. sp. radicicola), Fusarium wilt (Fusarium oxysporum f. sp.adzukicola), Fusarium basal rot (Fusarium oxysporum f. sp. allii, F.solani f. sp. radicicola), Stem rot (Fusarium oxysporum f. sp. batatas,F. solani), Dry rot (Fusarium oxysporum f. sp. colocasiae), Yellows(Fusarium oxysporum f. sp. conglutinans), Panama disease (Fusariumoxysporum f. sp. cubense), Fusarium wilt (Fusarium oxysporum f. sp.fragariae), Root rot (Fusarium oxysporum f. sp. lactucae), Fusarium wilt(Fusarium oxysporum f. sp. lagenariae, F. o.f. sp. niveum), Fusariumwilt (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt (Fusariumoxysporum f. sp. melonis), Yellows (Fusarium oxysporum f. sp. raphani),Fusarium wilt (Fusarium oxysporum f. sp. spinaciae),

“Bakanae” disease (Gibberella fujikuroi), Verticillium black spot(Verticillium albo-atrum, V. dahliae), Verticillium wilt (Verticilliumdahliae), Ceratocystis canker (Ceratocystis ficicola), Black rot(Ceratocystis fimbriata), Gray blight (Pestalotiopsis longiseta, P.theae), Endothia canker (Cryphonectria parasitica), Melanose (Diaporthecitri), Stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsisfukushii), Brown spot (Phomopsis vexans), Anthracnose (Disculatheae-sinensis), Valsa canker (Valsa ceratosperma), Blast (Magnaporthegrisea), Crown rot (Colletotrichum acutatum, C. fragariae, Glomerellacingulata), Bitter rot (Colletotrichum acutatum, Glomerella cingulata),Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Anthracnose(Colletotrichum acutatum), Ripe rot (Colletotrichum acutatum, Glomerellacingulata), Anthracnose (Colletotrichum acutatum), Anthracnose(Colletotrichum lindemuthianum), Anthracnose (Colletotrichumorbiculare), Anthracnose (Glomerella cingulata), Anthracnose (Glomerellacingulata), Anthracnose (Glomerella cingulata), Brown stem rot(Phialophora gregata), Leaf spot (Pseudophloeosporella dioscoreae),Scald (Rhynchosporium secalis),Rust (Phakopsora nishidana), Rust (Phakopsora pachyrhizi), Rust(Kuehneola japonica, Phraqmidium fusiforme, P. mucronatum, P.rosae-multiflorae), Rust (Gymnosporangium asiaticum), Rust(Gymnosporangium yamadae), Rust (Puccinia allii), Rust (Pucciniahoriana), Brown rust (Puccinia recondita), Rust (Puccinia tanaceti var.tanaceti), Rust (Uromyces viciae-fabae var. viciae-fabae), Smut(Sporisorium scitamineum), Smut (Ustilago maydis), Loose smut (Ustilagonuda), Net blister blight (Exobasidium reticulatum), Blister blight(Exobasidium vexans), Stem rot, Southern blight (Athelia rolfsii), Rootand stem rot (Ceratobasidium cornigerum, Rhizoctonia solani),(Rhizoctonia solani), Damping-off (Rhizoctonia solani), Damping-off(Rhizoctonia solani), Bottom rot (Rhizoctonia solani), Brown patch,Large patch (Rhizoctonia solani), Sheath blight (Thanatephoruscucumeris), Root rot/Leaf blight (Thanatephorus cucumeris), Rhizopus rot(Rhizopus stolonifer var. stolonifer), Clubroot (Plasmodiophorabrassicae), Aphanomyces root rot (Aphanomyces cochlioides), White rust(Albugo macrospora), Downy mildew (Bremia lactucae), Downy mildew(Peronospora chrysanthemi-coronarii), Downy mildew (Peronosporadestructor), Downy mildew (Peronospora farinosa f. sp. spinaciae), Downymildew (Peronospora manshurica), Downy mildew (Peronospora parasitica),Downy mildew (Peronospora sparsa), Downy mildew (Plasmopara halstedii),Downy mildew (Plasmopara nivea), Downy mildew (Plasmopara viticola),Downy mildew (Pseudoperonospora cubensis), Phytophthora root rot(Phytophthora cactorum), Brown rot (Phytophthora capsici), Phytophthorarot (Phytophthora capsici), Phytophthora blight (Phytophthora capsici),Phytophthora rot (Phytophthora cryptogea), Late blight (Phytophthorainfestans), White powdery rot (Phytophthora palmivora), Leaf blight(Phytophthora porri), Phytophthora root and stem rot (Phytophthorasoiae), Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola),Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P.ultimum var. ultimum), Root rot (Pythium aristosporum), Browning rootrot (Pythium arrhenomanes, P. graminicola), Damping-off (Pythiumbuismaniae, P. myriotylum), Root rot (Pythium myriotylum), Root rot(Pythium myriotylum, P. ultimum var. ultimum), Brown blotted root rot(Pythium sulcatum), Bacterial canker (Clavibacter michiganensis subsp.michiqanensis), Scab (Streptomyces spp.),Crown gall (Rhizobium radiobacter), Bacterial stripe (Burkholderiaandropogonis), Soft rot (Burkholderia cepacia, Pseudomonas marqinalismarqinalis, Erwinia rhapontici), Bacterial grain rot (Burkholderiagladioli, B. glumae), Bacterial fruit blotch (Acidovorax avenae subsp.citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt(Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricolapv. pruni, Pseudomonas syrinqae pv. syrinqae, Brenneria niqrifluens),Bacterial leaf spot (Xanthomonas arboricola a. pruni), Bacterial spot(Xanthomonas axonopodis a. vitians), Black rot (Xanthomonas campestrispv. campestris), Bacterial pustule (Xanthomonas campestris pv.glycines), Bacterial spot (Xanthomonas campestris pv. nigromaculans),Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker(Xanthomonas citri subsp. citri), (Pseudomonas cichorii, P. marqinalisa. marqinalis, Erwinia sp.), Bacterial rot (Pseudomonas cichorii, P.marginalis a. marqinalis, P. viridiflava), Bacterial blossom blight(Pseudomonas marginalis pv. marqinalis, P. syrinqae pv. syringae, P.viridiflava), Bacterial canker (Pseudomonas syrinqae pv. actinidiae),Canker (Pseudomonas syringae a. eriobotryae), Bacterial spot(Pseudomonas syringae lachrymans), Bacterial black spot (Pseudomonassyringae pv. maculicola), Bacterial canker (Pseudomonas syringae pv.morsprunorum, Erwinia sp.), Bacterial shoot blight (Pseudomonas syrigaea. theae), Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum),Fire blight (Erwinia amylovora), Soft rot (Pectobacterium carotovorum),Bacterial soft rot (Pectobacterium carotovorum).

Animal Diseases:

Pneumocystis pneumonia (Pneumocystis jirovecii), Candidiasis (Candidaalbicans), Aspergillosis (Aspergillus fumiqatus), Trichophytosis(Microsporum canis, M. gypseum, Trichophyton mentagrophytes, T. rubrum,T. tonsurans, T. verrucosum), Histoplasmosis (Histoplasma capsulatum),Cryptococcosis (Cryptococcus neoformans).

Parasites herein mean plant-parasitic nematodes parasitizing plants,animal-parasitic nematodes parasitizing animals, Acanthocephala,Platyhelminthes, Protozoa and the like, and specifically, the followingparasites may, for example, be mentioned, but the present invention isnot restricted thereto.

Nematodes of the order Enoplida such as Giant kidney worm (Dioctophymarenale), Thread worms (Capillaria annulata), Cropworm (Capillariacontorta), Capillary liver worm (Capillaria hepatica), Capillariaperforans, Capillaria philippinensis, Capillaria suis, Whipworm(Trichuris discolor), Whipworm (Trichuris ovis), Pig whipworm (Trichurissuis), Human whipworm (Trichuris trichiura), Dog whipworm (Trichurisvulpis), Pork worm (Trichinella spiralis), etc.

Nematodes of the order Rhabditida such as Intestinal threadworm(Strongyloides papillosus), Strongyloides planiceps, Pig threadworm(Strongyloides ransomi), Threadworm (Strongyloides stercoralis),Micronema spp., etc.

Nematodes of the order Strongylida such as Hookworm (Ancylostomabraziliense), Dog hookworm (Ancylostoma caninum), Old World hookworm(Ancylostoma duodenale), Cat hookworm (Ancylostoma tubaeforme), TheNorthern hookworm of dogs (Uncinaria stenocephala), Cattle hookworm(Bunostomum phlebotomum), Small ruminant hookworm (Bunostomumtrigonocephalum), New World hookworm (Necator americanus), Cyathostomumspp., Cylicocyclus spp., Cylicodontophorus spp., Cylicostephanus spp.,Strongylus asini, Stronqylus edentatus, Blood worm (Stronqylus equinus),Blood worm (Strongylus vulgaris), Large-mouthed bowel worm (Chabertiaovina), Nodular worm (Oesophagostomum brevicaudatum), Nodule worm(Oesophagostomum columbianum), Nodule worm (Oesophagostomum dentatum),Nodular worm (Oesophagostomum georgianum), Nodular worm (Oesophagostomummaplestonei), Nodular worm (Oesophagostomum quadrispinulatum), Nodularworm (Oesophagostomum radiatum), Nodular worm (Oesophagostomumvenulosum), Syngamus skrjabinomorpha, Gapeworm (Syngamus trachea), Swinekidney worm (Stephanurus dentatus), Cattle bankrupt worm (Cooperiaoncophora), Red stomach worm (Hyostrongylus rubidus), Stomach hair worm(Trichostrongylus axei), Trichostrongylus colubriformis, Orientaltrichostrongylus (Trichostrongylus orientalis), Red stomach worm(Haemonchus contortus), Cattle stomach worm (Mecistocirrus digitatus),Brown stomach worm (Ostertagia ostertaqi), Common lungworm (Dictyocaulusfilaria), Bovine lungworm (Dictyocaulus viviparus), Thin-neckedintestinal worm (Nematodirus filicollis), Swine lungworm (Metastrongyluselongatus), Lungworm (Filaroides hirthi), Lungworm (Crenosomaaerophila), Fox lungworm (Crenosoma vulpis), Rat lung worm(Angiostrongylus cantonensis), French heartworm (Angiostrongylusvasorum), Protostrongylus spp., etc.

Nematodes of the order Aphelenchida such as Rice white tip nematode(Aphelenchoides besseyi), Strawberry foliar nematode (Aphelenchoidesfragariae), Chrysanthemum foliar nematode (Aphelenchoides ritzemabosi),Pine wood nematode (Bursaphelenchus xylophilus), etc.

Nematodes of the order Tylenchida such as White potato cyst nematode(Globodera pallida), Potato cyst nematode (Globodera rostochiensis),Cereal cyst nematode (Heterodera avenae), Soybean cyst nematode(Heterodera glycines), Sugarbeet cyst nematode (Heterodera schachtii),Clover cyst nematode (Heterodera trifolii), Peanut root-knot nematode(Meloidogyne arenaria), Northern root-knot nematode (Meloidogyne hapla),Southern root-knot nematode (Meloidogyne incognita), Javanese root-knotnematode (Meloidogyne iavanica), Apple root-knot nematode (Meloidogynemali), Coffee root-lesion nematode (Pratylenchus coffeae), (Pratylenchusdrenatus), Tea root-lesion nematode (Pratylenchus loosi), Californiaroot-lesion nematode (Pratylenchus neglectus), Cobb's root-lesionnematode (Pratylenchus penetrans), Walnut root-lesion nematode(Pratylenchus vulnus), Citrus burrowing nematode (Radopholuscitrophilus), Banana burrowing nematode (Radopholus similis), etc.

Nematodes of the order Oxyurida such as Pinworm (Enterobiusvermicularis), Equine pinworm (Oxyuris equi), Rabbit pinworm (Passalurusambiguus), etc.

Nematodes of the order Ascaridida such as Pig roundworm (Ascaris suum),Horse roundworm (Parascaris equorum), Dog roundworm (Toxascarisleonina), Dog intestinal roundworm (Toxocara canis), Feline roundworm(Toxocara cati), Large cattle roundworm (Toxocara vitulorum), Anisakisspp., Pseudoterranova spp., Caecal worm (Heterakis gallinarum), Chickenroundworm (Ascaridia galli), etc.

Nematodes of the order Spirurida such as Guinea worm (Dracunculusmedinensis), Gnathostoma doloresi, Gnathostoma hispidum, Gnathostomanipponicum, Reddish-coloured worm (Gnathostoma spinigerum), Dog stomachworm (Physaloptera canis), Cat stomach worm (Physaloptera felidis, P.praeputialis), Feline/canine stomach worm (Physaloptera rara), Eye worm(Thelazia callipaeda), Bovine eyeworm (Thelazia rhodesi), Large mouthstomach worm (Draschia megastoma), Equine stomach worm (Habronemamicrostoma), Stomach worm (Habronema muscae), Gullet worm (Gongylonemapulchrum), Thick stomach worm (Ascarops strongylina), Parafilaria(Parafilaria bovicola), Parafilaria multipapillosa, Stephanofilariaokinawaensis, Bancroft filarial (Wuchereria bancrofti), Brugia malayi,Neck threadworm (Onchocerca cervicalis), Onchocerca gibsoni, Cattlefilarial worm (Onchocerca qutturosa), Onchocerca volvulus, Bovinefilarial worm (Setaria digitata), Peritoneal worm (Setaria equina),Setaria labiatopapillosa, Setaria marshalli, Dog heartworm (Dirofilariaimmitis), African eye worm (Loa loa), etc.

Microorganisms of the phylum Acanthocephala such as Moniliformismoniliformis, Giant thorny-headed worm (Macracanthorhynchushirudinaceus), etc.

Cestodes of the order Pseudophyllidea such as Fish tapeworm(Diphyllobothrium latum), Diphyllobothrium nihonkaiense, Manson tapeworm(Spirometra erinaceieuropaei), Diplogonoporus grandis, etc.

Cestodes of the order Cyclophyllidea such as (Mesocestoides lineatus),Chicken tapeworm (Raillietina cesticillus), Fowl tapeworm (Raillietinaechinobothrida), Chicken tapeworm (Raillietina tetragona), Caninetapeworm (Taenia hydatiqena), Canine tapeworm (Taenia multiceps), Sheepmeasles (Taenia ovis), Dog tapeworm (Taenia pisiformis), Beef tapeworm(Taenia saginata), Tapeworm (Taenia serialis), Pork tapeworm (Taeniasolium), Feline tapeworm (Taenia taeniaeformis), Hydatid tapeworm(Echinococcus granulosus), Small fox tapeworm (Echinococcusmultilocularis), Echinococcus oligarthrus, Echinococcus vogeli, Rattapeworm (Hymenolepis diminuta), Dwarf tapeworm (Hymenolepis nana),Double-pored dog tapeworm (Dipylidium caninum), Amoebotaenia sphenoides,Choanotaenia infundibulum, Metroliasthes coturnix, Equine tapeworm(Anoplocephala magna), Cecal tapeworm (Anoplocephala perfoliata), Dwarfequine tapeworm (Paranoplocephala mamillana), Common tapeworm (Monieziabenedeni), Sheep tapeworm (Moniezia expansa), Stilesia spp., etc.

Trematodes of the order Strigeidida such as Pharyngostomum cordatum,Blood fluke (Schistosoma haematobium), Blood fluke (Schistosomajaponicum), Blood fluke (Schistosoma mansoni), etc.

Trematodes of the order Echinostomida such as Echinostoma cinetorchis,Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Commonliver fluke (Fasciola hepatica), Fasciolopsis buski, Homalogasterpaloniae, etc.

Trematodes of the order Plagiorchiida such as Dicrocoelium chinensis,Lancet liver fluke (Dicrocoelium dendriticum), African lancet fluke(Dicrocoelium hospes), Eurytrema coelomaticum, Pancreatic fluke(Eurytrema pancreaticum), Paragonimus miyazakii, Paraqonimus ohirai,Lung fluke (Paragonimus westermani), etc.

Trematodes of the order Opisthorchiida such as Amphimerus spp., Chineseliver fluke (Clonorchis sinensis), Cat liver fluke (Opisthorchisfelineus), Southeast Aasian liver fluke (Opisthorchis viverrini),Pseudamphistomum spp., Metorchis spp., Parametorchis spp., Intestinalfluke (Heterophyes heterophyes), Metaqonimus yokokawai, Pyqidiopsissumma, etc.

Amebas such as Entamoeba histolytica, E. invadens, etc.

Piroplasmida sporozoa such as Babesia biqemina, Babesia bovis, Babesiacaballi, Babesia canis, Babesia felis, Babesia gibsoni, Babesia ovata,Cytauxzoon felis, Theileria annulata, Theileria mutans, Theileriaorientalis, Theileria parva, etc.

Haemosporida sporozoa such as Haemoproteus mansoni, Leucocytozooncaulleryi, Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale,Plasmodium vivax, etc.

Eucoccidiorida sporozoa such as Caryospora spp., Eimeria acervulina,Eimeria bovis, Eimeria brunet, Eimeria maxima, Eimeria necatrix, Eimeriaovinoidalis, Eimeria stiedae, Eimeria tenella, Isospora canis, Isosporafelis, Isospora suis, Tyzzeria alleni, Tyzzeria anseris, Tyzzeriaperniciosa, Wenyonella anatis, Wenyonella gagari, Cryptosporidium canis,Cryptosporidium felis, Cryptosporidium hominis, Cryptosporidiummeleaqridis, Cryptosporidium muris, Cryptosporidium parvum, Sarcocystiscanis, Sarcocystis cruzi, Sarcocystis felis, Sarcocystis hominis,Sarcocystis miescheriana, Sarcocystis neurona, Sarcocystis tenella,Sarcocystis ovalis, Toxoplasma gondii, Hepatozoon canis, Hepatozoonfelis, etc.

Vestibuliferida Ciliata such as Balantidium coli, etc.

Trichomonadida flagellata such as Histomanas meleagridis,Pentatrichomonas hominis, Trichomonas tenax, etc.

Diplomonadida flagellata such as Giardia intestinalis, Giardia muris,Hexamita meleagridis, Hexamita parva, etc.

Kinetoplastida flagellata such as Leishmania donovani, Leishmaniainfantum, Leishmania maior, Leishmania tropica, Trypanosoma bruceigambiense, Trypanosoma brucei rhodesiense, Trypanosoma cruzi,Trypanosoma equiperdum, Trypanosoma evansi, etc.

Useful insects herein mean insects useful for human life by utilizingtheir products, or useful to make agricultural work efficient e.g. byusing them for pollination of orchard trees/vegetables, andspecifically, Japanese honeybee (Apis cerana japonica), Western honeybee (Apis mellifera), Bumblebee (Bombus consobrinus wittenburgi, B.diversus diversus, B. hypocrita hypocrita, B. ignitus, B. terrestris),Hornfaced bee (Osmia cornifrons), Silkworm (Bombyx mori) may, forexample, be mentioned, but the present invention is not restrictedthereto.

Natural enemies herein mean organisms which kill specific organismsparticularly specific organisms damaging agricultural crops by predationor parasitism or which inhibit propagation of such organisms, andspecifically, the following organisms may, for example, be mentioned,but the present invention is not restricted thereto.

Parasitic wasps belonging to the family Braconidae such as Dacnusasasakawai, Dacnusa sibirica, Aphidius colemani, Apanteles glomeratus,etc., the family Aphelimidae such as Aphelinus albipodus, Aphelinusasychis, Aphelinus gossypii, Aphelinus maculatus, Aphelinus varipes,Encarsia formosa, Eretmocerus eremicus, Eretmocerus mundus, etc., andthe family Eulophidae such as Chrysocharis pentheus, Neochrysocharisformosa, Diglyphus isaea, Hemiptarsenus varicornis, etc.; Aphidophagousgall midge (Aphidoletes aphidimyza); Seven-spot ladybird (Coccinellaseptempunctata); Asian lady beetle (Harmonia axyridis); Predatory beetle(Propylea japonica); Anthocorid predatory bugs belonging to the familyAnthocoridae such as Orius minutus, Orius nagaii, Orius sauteri, Minutepirate bug (Orius strigicollis), etc.; Predatory mirids belonging to thefamily Miridae such as Pilophorus typicus, Nesidiocoris tenuis, etc.;Predatory thrips belonging to the family Aeolothripidae such asFranklinothrips vespiformis, etc.; Green lacewing belonging to thefamily Chrysopidae such as Dichochrysa formosanus, Chrysoperlanipponensis, etc.; Predatory mites belonging to the family Phytoseiidaesuch as Neoseiulus californicus, Amblyseius cucumeris, Amblyseiusdegenerans, Amblyseius swirskii, Phytoseiulus persimilis, etc.; Wolfspider (Pardosa pseudoannulata); Crab spider (Misumenops tricuspidatus).

The compounds of the present invention represented by the formula (I)can be produced, for example, by the following processes.

A compound represented by the formula (II) [wherein G², R¹, R² and R³are the same as defined above] or its salt (such as a hydrochloride or ahydrobromide) is reacted with a compound represented by the formula(III) [wherein G¹ is the same as defined above, and J¹ is a chlorineatom, a bromine atom, a C₁-C₄ alkylcarbonyloxy group (such as apivaloyloxy group), a C₁-C₄ alkoxycarbonyloxy group (such as anisobutyloxycarbonyloxy group), an azolyl group (such as an imidazol-1-ylgroup) or the like], if necessary in a solvent such as benzene, toluene,dichloromethane, chloroform, 1,2-dichloroethane, diethyl ether,tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate,N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, water or amixture of two or more of them in an any ratio, if necessary in thepresence of a base such as sodium carbonate, potassium carbonate, sodiumhydrogen carbonate, sodium acetate, triethylamine, ethyldiisopropylamine, N-methylmorpholine, pyridine or4-(dimethylamino)pyridine in an amount of from 1 to 3 equivalents per 1equivalent of the compound represented by the formula (II), within atemperature range of from 0° C. to the refluxing temperature of thereaction mixture for from 30 minutes to 24 hours, to obtain a compoundof the present invention represented by the formula (Ia) [wherein G¹,R¹, R² and R³ are the same as defined above] which is a compound of theformula (I) wherein W is an oxygen atom, and R⁴ is a hydrogen atom.

Some of the compounds represented by the formula (III) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature, for example, by a method inaccordance with the method disclosed in J. Med. Chem., 1991, vol. 34, p.1630, etc., in which a corresponding known carboxylic acid is reactedwith a halogenating agent such as thionyl chloride, phosphoruspentachloride or oxalyl chloride, a method in accordance with the methoddisclosed in Tetrahedron Letters, 2003, vol. 44, p. 4819, J. Med. Chem.,1991, vol. 34, p. 222, etc., in which a corresponding known carboxylicacid is reacted with an organic acid halide such as pivaloyl chloride orisobutyl chloroformate in the presence of a base if necessary, or amethod disclosed in J. Org. Chem., 1989, vol. 54, p. 5620, etc., inwhich a corresponding known carboxylic acid is reacted with carbonyldiimidazole, sulfonyl diimidazole or the like.

1 Equivalent of a compound represented by the formula (IV) [wherein G¹,G², W, R², R³ and R⁴ are the same as defined above] is reacted with from1 to 3 equivalents of a compound represented by the formula (V) [whereinR¹ is the same as defined above] or its salt (such as a hydrochloride ora hydrobromide), if necessary in a solvent such as benzene, toluene,methanol, ethanol, tetrahydrofuran, acetic acid, pyridine, water or amixture of two or more of them in any ratio, if necessary in thepresence of a base such as sodium hydroxide, potassium hydroxide, sodiumcarbonate, potassium carbonate, sodium hydrogen carbonate, sodiumacetate, triethylamine or pyridine in an amount of from 1 to 4equivalents per 1 equivalent of the compound represented by the formula(IV), or with hydrochloric acid, sulfuric acid or the like as a catalystin an amount of from 0.1 to 1 equivalent per 1 equivalent of thecompound represented by the formula (IV), within a temperature range offrom room temperature to the refluxing temperature of the reactionmixture for from 1 to 48 hours to obtain a compound of the presentinvention represented by the formula (I) [wherein G¹, G², W, R¹, R², R³and R⁴ are the same as defined above].

1 Equivalent of a compound represented by the formula (IV) [wherein G¹,G², W, R², R³ and R⁴ are the same as defined above] and from 1 to 3equivalents of hydroxylamine or its salt (such as a hydrochloride or asulfate) are reacted, if necessary in a solvent such as methanol,ethanol, 1,4-dioxane, acetonitrile, pyridine, water or a mixture of twoor more of them in any ratio, if necessary in the presence of a basesuch as sodium hydroxide, potassium hydroxide, sodium carbonate,potassium carbonate, sodium hydrogen carbonate, sodium acetate,ethyldiisopropylamine or pyridine in an amount of from 1 to 4equivalents per 1 equivalent of the compound represented by the formula(IV), within a temperature range of from room temperature to therefluxing temperature of the reaction mixture for from 1 to 24 hours toobtain a compound represented by the formula (VI) [wherein G¹, G², W,R², R³ and R⁴ are the same as defined above]. 1 Equivalent of theobtained compound represented by the formula (VI) and from 1 to 10equivalents of a compound represented by the formula (VII) [wherein R¹is the same as defined above, J² is a chlorine atom, a bromine atom, aniodine atom, a C₁-C₄ alkylsulfonate group (such as a methanesulfonyloxygroup), a C₁-C₄ haloalkylsulfonate group (such as atrifluoromethanesulfonyloxy group) or the like] are reacted, ifnecessary in an atmosphere of an inert gas such as nitrogen or argon, ifnecessary in a solvent such as benzene, toluene, dichloromethane,chloroform, tetrahydrofuran, acetone, acetonitrile,N,N-dimethylformamide, dimethylsulfoxide, water or a mixture of two ormore of them in any ratio, if necessary in the presence of a base suchas sodium hydride, sodium methoxide, sodium ethoxide, sodium hydroxide,potassium hydroxide, sodium carbonate, potassium carbonate, cesiumcarbonate or triethylamine in an amount of from 1 to 3 equivalents per 1equivalent of the compound represented by the formula (VI), if necessarywith tetrabutylammonium bromide, potassium iodide or the like as acatalyst in an amount of from 0.01 to 1 equivalent per 1 equivalent ofthe compound represented by the formula (VI), within a temperature rangeof from room temperature to the refluxing temperature of the reactionmixture for from 1 to 24 hours to obtain a compound of the presentinvention represented by the formula (I) [wherein G¹, G², W, R¹, R², R³and R⁴ are the same as defined above].

The compounds represented by the formula (VII) used in this process areknown compounds, and some of them are commercially available. The restof them can be synthesized in accordance with known methods disclosed inthe literature regarding known compounds.

A compound represented by the formula (VIII) [wherein G¹, G², W, R², R³and R⁴ are the same as defined above] is reacted, for example, withsodium nitrite by a method in accordance with J. Org. Chem., 2004, vol.69, p. 8997, etc., with tin(II) chloride-phenylmercaptan by a method inaccordance with Tetrahedron, 1990, vol. 46, p. 587, etc., or with carbondisulfide by a method in accordance with J. Org. Chem., 1983, vol. 48,p. 2766, etc., to obtain a compound represented by the formula (VI)[wherein G¹, G², W, R², R³ and R⁴ are the same as defined above].

The compound represented by formula (VI) thus obtained may be reactedwith a compound represented by the formula (VII) [wherein R¹ and J² arethe same as defined above] in the same manner as in process C to obtaina compound of the present invention represented by the formula (I)[wherein G¹, G², W, R¹, R², R³ and R⁴ are the same as defined above].

1 Equivalent of a compound of the present invention represented by theformula (Ia) [wherein G¹, G², R¹, R² and R³ are the same as definedabove] which is a compound of the formula (I) wherein W is an oxygenatom and R⁴ is a hydrogen atom, is reacted with from 1 to 10 equivalentsof a compound represented by the formula (IX) [wherein R⁴ is the same asdefined above except for a hydrogen atom, and J³ is a favorable leavinggroup such as a chlorine atom, a bromine atom, an iodine atom, a C₁-C₄alkylcarbonyloxy group (such as a pivaloyloxy group), a C₁-C₄alkylsulfonate (such as a methanesulfonyloxy group), a C₁-C₄haloalkylsulfonate group (such as a trifluoromethanesulfonyloxy group),an arylsulfonate group (such as a benzenesulfonyloxy group or ap-toluenesulfonyloxy group), an azolyl group (such as an imidazol-1-ylgroup) or the like], if necessary in a polar solvent such as tert-butylmethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile orN,N-dimethylformamide, if necessary in the presence of a base such assodium hydride, potassium tert-butoxide, potassium hydroxide, potassiumcarbonate, triethylamine or pyridine in an amount of from 1 to 3equivalents per 1 equivalent of the compound represented by the formula(Ia), within a temperature range of from 0 to 90° C. for from 10 minutesto 24 hours to obtain a compound of the present invention represented bythe formula (Ib) [wherein G¹, G², R¹, R² and R³ are the same as definedabove, and R⁴ is the same as defined above except for a hydrogen atom]which is a compound of the formula (I) wherein W is an oxygen atom.

Some of the compounds represented by the formula (IX) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature regarding known compounds, forexample, the method disclosed in Chem. Pharm. Bull., 1986, vol. 34, p.540 and 2001, vol. 49, p. 1102, J. Am. Chem. Soc., 1964, vol. 86, p.4383, J. Org. Chem., 1983, vol. 48, p. 5280, Org. Synth., 1988,collective vol. 6, p. 101, Synlett, 2005, p. 2847, Synthesis, 1990, p.1159, JP05/125017, EP0,051,273, GB2,161,802 or the like.

1 Equivalent of a compound of the present invention represented by theformula (Ib) [wherein G¹, G², R¹, R², R³ and R⁴ are the same as definedabove] which is a compound of the formula (I) wherein W is an oxygenatom, and from 1 to 10 equivalents of a sulfidizing agent such asphosphorus pentasulfide, phosphorus pentasulfide-HMDO(hexamethyldisiloxane) or Lawesson's Reagent(2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane=2,4-disulfide) arereacted, if necessary in a solvent such as benzene, toluene,chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or HMPA, if necessary in the presence of abase such as sodium hydrogen carbonate, triethylamine or pyridine in anamount of from 1 to 4 equivalents per 1 equivalent of the compoundrepresented by the formula (Ib), within a temperature range of from roomtemperature to the refluxing temperature of the reaction mixture forfrom 10 minutes to 50 hours, or in pyridine as a base in an amountsufficient as a solvent within a temperature range of from 80° C. to therefluxing temperature of the reaction mixture for from 1 to 3 hours, toobtain a compound of the present invention represented by the formula(Ic) [wherein G¹, G², R¹, R², R³ and R⁴ are the same as defined above]which is a compound of the formula (I) wherein W is a sulfur atom.

In processes A to F, the reaction mixture after a reaction can be workedup by an ordinary procedure such as direct concentration, a proceduresuch that the reaction mixture is dissolved in an organic solvent,washed with water and concentrated, or a procedure such that thereaction mixture is poured into ice water, extracted with an organicsolvent and concentrated, to obtain the desired oxime-substituted amidecompound. If purification is needed, the desired oxime-substituted amidecompound may be isolated or purified by an optional purification methodsuch as recrystallization or fractionation by column chromatography,thin layer chromatography or liquid chromatography.

The compound represented by the formula (II) used in process A may besynthesized, for example, by reaction schemes 1 to 3.

1 Equivalent of a compound represented by the formula (X) [wherein G²,R² and R³ are the same as defined above, and J⁴ is a chlorine atom,bromine atom, an iodine atom or the like] and from 1 to 1.5 equivalentsof potassium phthalimide are reacted, in a solvent such as toluene,dichloromethane, tetrahydrofuran, 1,4-dioxane, acetone,N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, ifnecessary in the presence of from 0.1 to 2 equivalents of a base such assodium carbonate, potassium carbonate or sodium hydrogen carbonate, ifnecessary with from 0.1 to 1 equivalent of tetrabutylammonium iodide,tributylhexadecylphosphonium bromide, crown ether (18-Crown-6) or thelike as a catalyst, within a temperature range of from room temperatureto the refluxing temperature of the reaction mixture for from 0.5 to 24hours to obtain a compound represented by the formula (XI) [wherein G²,R² and R³ are the same as defined above]. The obtained compoundrepresented by the formula (XI) is reacted with a compound representedby the formula (V) [wherein R¹ is the same as defined above] under thesame conditions as in process B to obtain a compound represented by theformula (XII) [wherein G², R¹, R² and R³ are the same as defined above].

Then, the compound represented by the formula (XII) is reacted withhydrazine monohydrate or aqueous hydrazine in an amount of from 1 to 4equivalents per 1 equivalent of the compound represented by the formula(XII), if necessary in a solvent such as toluene, dichloromethane,chloroform, methanol, ethanol, tetrahydrofuran, 1,4-dioxane, water or amixture of two or more of them in any ratio, if necessary in anatmosphere of an inert gas such as nitrogen or argon, within atemperature range of from room temperature to the refluxing temperatureof the reaction mixture for from 1 to 24 hours to obtain a compoundrepresented by the formula (II) [wherein G², R¹, R² and R³ are the sameas defined above].

Some of the compounds represented by the formula (X) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature regarding known compounds.

A compound represented by the formula (X) [wherein G², R², R³ and J⁴ arethe same as defined above] and the compound represented by the formula(V) [wherein R¹ is the same as defined above] are reacted under the sameconditions as in process B to obtain a compound represented by theformula (XIII) [wherein G², R¹, R², R³ and J⁴ are the same as definedabove], and the obtained compound represented by the formula (XIII) isreacted with potassium phthalimide in the same manner as in reactionscheme 1 to obtain a compound represented by the formula (XII) [whereinG², R¹, R² and R³ are the same as defined above].

Then, the compound represented by the formula (XII) is reacted withhydrazine monohydrate or aqueous hydrazine in the same manner as inreaction scheme 1 to obtain a compound represented by the formula (II)[wherein G², R¹, R², and R³ are the same as defined above].

A known compound represented by the formula (XIV) [wherein G² is thesame as defined above, and J⁴ is a hydrogen atom, a chlorine atom, abromine atom, an iodine atom or the like] is reacted with analkyllithium, a Grignard reagent or the like in accordance with a methoddisclosed in Tetrahedron Lett., 2002, vol. 43, p. 8223 and 2005, vol.46, p. 8587, J. Org. Chem., 2006, vol. 71, p. 9861, etc., to prepare acompound represented by the formula (XV) [wherein G² is the same asdefined above, and M is Li, MgCl, MgBr, MgI or the like], and theprepared compound represented by the formula (XV) and a compoundrepresented by the formula (XVI) [wherein R² and R³ are the same asdefined above, R is a tert-butyl group, a benzyl group or the like, andJ⁵ is a dimethylamino group, a N-methylmethoxyamine group, apiperidin-1-yl group, a benzotriazol-1-yl group or the like] are reactedto obtain a compound represented by the formula (XVII) [wherein G², R²,R³ and R are the same as defined above].

Some of the compounds represented by the formula (XVI) are knowncompounds, and some of them are commercially available. The rest of themcan be synthesized in accordance with known methods disclosed in theliterature regarding known compounds.

Then, the compound represented by the formula (XVII) and a compoundrepresented by the formula (V) [wherein R¹ is the same as defined above]are reacted under the same conditions as in process B to obtain acompound represented by the formula (XVIII) [wherein G², R¹, R², R³ andR are the same as defined above]. The obtained compound represented bythe formula (XVIII) is deprotected under known reaction conditions withrespect to the substituent R to obtain a compound represented by theformula (II) [wherein G², R¹, R², and R³ are the same as defined above]or its salt (such as a hydrochloride, a hydrobromide, a trifluoroacetateor a p-toluenesulfonate).

The compound represented by the formula (IV) used in processes B and Cmay be synthesized, for example, by reaction scheme 4 or 5.

A compound represented by the formula (III) [wherein G¹ and J¹ are thesame as defined above] and a compound represented by the formula (XIX)[wherein G², R² and R³ are the same as defined above, and R⁴ is ahydrogen atom, a C₁-C₆ alkyl group or the like] or its salt (such as ahydrochloride, a hydrobromide, a trifluoroacetate or ap-toluenesulfonate) are reacted under the same conditions as in processA to obtain a compound represented by the formula (IVb) [wherein G¹, G²,R² and R³ are the same as defined above, and R⁴ is a hydrogen atom, aC₁-C₆ alkyl group or the like] which is a compound of the formula (IV)wherein W is an oxygen atom.

A compound represented by the formula (XX) [wherein G¹, R², R³ and R⁴are the same as defined above] is reacted for example by a methoddisclosed in J. Med. Chem., 2004, vol. 47, p. 6884, Bioorganic & Med.Chem. Lett., 2012, vol. 22, p. 5485, etc. to prepare a compoundrepresented by the formula (XXI) [wherein G¹, R², R³, R⁴ and J⁵ are thesame as defined above], and the obtained compound represented by theformula (XXI) is reacted with a compound represented by the formula (XV)[wherein G² and M are the same as defined above] in the same manner asin reaction scheme 3 to obtain a compound represented by the formula(IVb) [wherein G¹, G², R² and R³ are the same as defined above, and R⁴is a hydrogen atom, a C₁-C₆ alkyl group or the like] which is a compoundof the formula (IV) wherein W is an oxygen atom.

Some of the compounds represented by the formula (XX) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature regarding known compounds.

Some of the compounds represented by the formula (V) used in process Bare known compounds, and some of them are commercially available. Therest of them can be synthesized, for example, as follows.

That is, N-hydroxyphthalimide and a compound represented by the formula(XXII) [wherein R¹ is the same as defined above, and J⁶ is a chlorineatom, a bromine atom, an iodine atom or hydroxy group] are reacted, forexample, in accordance with a method disclosed in J. Med. Chem., 2008,vol. 51, p. 4601, WO2008/055013, etc. to obtain a compound representedby the formula (XXIII) [wherein R¹ is the same as defined above], andthe obtained compound represented by the formula (XXIII) is reacted withhydrazine monohydrate or aqueous hydrazine under the same conditions asin reaction scheme 1 to obtain a compound represented by the formula (V)[wherein R¹ is the same as defined above].

Some of the compounds represented by the formula (XXII) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature regarding known compounds.

The compound represented by the formula (VIII) used in process D may besynthesized, for example, as follows.

That is, a compound represented by the formula (III) [wherein G¹ and J¹are the same as defined above] and a compound represented by the formula(XXIV) [wherein R⁴ is a hydrogen atom, a C₁-C₆ alkyl group or the like]or its salt (such as a hydrochloride) are reacted under the sameconditions as in process A to obtain a compound represented by theformula (XXV) [wherein G¹ is the same as defined above, and R⁴ is ahydrogen atom, a C₁-C₆ alkyl group or the like].

The primary amines represented by the formula (XXIV) used in thisprocess are known compounds, and some of them are commerciallyavailable. The rest of them can be synthesized in accordance with knownmethods disclosed in the literature regarding known primary amines.

Then, the obtained compound represented by the formula (XXV) is reacted,for example, in accordance with a method disclosed in WO2007/026965,Tetrahedron Lett., 1994, vol. 35, p. 7107, WO2006/067103, J. Org. Chem.,1987, vol. 52, p. 5475, etc. to obtain a compound represented by theformula (XXVI) [wherein G¹ is the same as defined above, R⁴ is ahydrogen atom, a C₁-C₆ alkyl group or the like, and J⁷ is a chlorineatom, a C₁-C₄ alkylcarbonyloxy group (such as an acetoxy group), a C₁-C₄alkylsulfonate group (such as a methanesulfonyloxy group) or anarylsulfonate group (such as a benzenesulfonyloxy group)].

The obtained compound represented by the formula (XXVI) and a compoundrepresented by the formula (XXVII) [wherein G² is the same as definedabove] are reacted, for example, in accordance with a method disclosedin Bull. Chem. Soc. Jpn., 2004, vol. 77, p. 2219, Tetrahedron Lett.,2006, vol. 47, p. 3501, J. Org. Chem., 2004, vol. 69, p. 8997, etc. toobtain a compound represented by the formula (VIIIb) [wherein G¹ and G²are the same as defined above, and R⁴ is a hydrogen atom, a C₁-C₆ alkylgroup or the like] which is the compound of the formula (VIII) wherein Wis an oxygen atom, and R² and R³ are hydrogen atoms.

The compound represented by the formula (XIX) may be produced bydeprotecting a compound represented by the formula (XVII) obtainable byreaction scheme 3 by a known method or may be synthesized, for example,by any of reaction schemes 8 to 11.

A compound represented by the formula (X) [wherein G², R², R³ and J⁴ arethe same as defined above] and hexamethylenetetramine are reacted, forexample, in accordance with a method disclosed in J. Heterocyclic Chem.,1987, vol. 24, p. 297 etc., if necessary in a solvent such as toluene,dichloromethane, chloroform, ethanol, diethyl ether, tetrahydrofuran,acetone, ethyl acetate, acetonitrile, water or a mixture of two or moreof them in any ratio, if necessary with sodium iodide or the like,within a temperature range of from room temperature to the refluxingtemperature of the reaction mixture for from 1 to 24 hours to obtain aquaternary ammonium salt represented by the formula (XXVIII) [whereinG², R², R³ and J⁴ are the same as defined above]. The obtainedquaternary ammonium salt represented by the formula (XXVIII) ishydrolyzed in a solvent such as methanol, ethanol, acetonitrile, wateror a mixture of two or more of them in any ratio, in the presence of anacid catalyst such as hydrochloric acid or hydrobromic acid within atemperature range of from room temperature to the refluxing temperatureof the reaction mixture for from 0.5 to 48 hours to obtain ahydrochloride or hydrobromide of a compound represented by the formula(XIXa) [wherein G², R² and R³ are the same as defined above] which is acompound of the formula (XIX) wherein R⁴ is a hydrogen atom. Further,after completion of the reaction, by neutralization with a base such assodium hydroxide or potassium hydroxide, a free amine may be isolated.

A compound represented by the formula (X) [wherein G², R², R³ and J⁴ arethe same as defined above] and sodium azide or lithium azide arereacted, for example, in accordance with a method disclosed in J. Org.Chem., 1986, vol. 51, p. 3374, etc., if necessary in a solvent such astoluene, methanol, tetrahydrofuran, acetone, N,N-dimethylformamide,acetonitrile, dimethylsulfoxide, water or a mixture of two or more ofthem in any ratio, if necessary with methyl trioctylammonium chloride,potassium iodide or the like as a catalyst, within a temperature rangeof from 0 to 50° C. for from 0.5 to 18 hours to obtain a compoundrepresented by the formula (XXIX) [wherein G², R² and R³ are the same asdefined above]. The obtained compound represented by formula (XXIX) ishydrogenated in a solvent such as methanol, ethanol, diethyl ether,water or a mixture of two or more of them in any ratio in the presenceof palladium or a platinum catalyst, if necessary with hydrochloric acidor the like, in an atmosphere of hydrogen under 1 to 10 atm at roomtemperature for from 0.5 to 24 hours; is reacted with a reducing agentsuch as tin(II) chloride in a solvent such as dichloromethane, methanol,ethanol or ethyl acetate within a temperature range of from roomtemperature to 60° C. for from 3 to 18 hours; or is reacted withtriphenylphosphine and water in a solvent such as tetrahydrofuran, wateror a mixture of the two in any ratio within a temperature range of from0° C. to room temperature for from 0.5 to 24 hours, to obtain a compound(XIXa) [wherein G², R² and R³ are the same as defined above] which is acompound of the formula (XIX) wherein R⁴ is a hydrogen atom. Further,after completion of the reaction if necessary, the compound of theformula (XIXa) may be treated with hydrochloric acid, hydrobromic acid,trifluoroacetic acid, p-toluenesulfonic acid or the like to obtain asalt thereof.

A compound represented by the formula (X) [wherein G², R², R³ and J⁴ arethe same as defined above] and diformylimide sodium salt are reacted,for example, in accordance with a method disclosed in Tetrahedron Lett.,1989, vol. 30, p. 5285 etc., in a solvent such as N,N-dimethylformamideor acetonitrile within a temperature range of from room temperature tothe refluxing temperature of the reaction mixture for from 2 to 24 hoursto obtain a compound represented by the formula (XXX) [wherein G², R²and R³ are the same as defined above]. The obtained compound representedby the formula (XXX) is hydrolyzed in a solvent such as methanol,ethanol, 1,4-dioxane, water or a mixture of two or more of them in anyratio with an acid such as hydrochloric acid within a temperature rangeof from room temperature to the refluxing temperature of the reactionmixture for from 1 to 24 hours to obtain a hydrochloride or the like ofa compound represented by the formula (XIXa) [wherein G², R² and R³ arethe same as defined above] which is a compound of the formula (XIX)wherein R⁴ is a hydrogen atom. Further, after completion of thereaction, by neutralization with a base such as sodium hydroxide orpotassium hydroxide, a free amine may be isolated.

A compound represented by the formula (X) [wherein G², R², R³ and J⁴ arethe same as defined above] and an amine represented by the formula(XXIV) [wherein R⁴ is a hydrogen atom, a C₁-C₆ alkyl group or the like]or its salt are reacted, if necessary in a solvent such as toluene,dichloromethane, methanol, ethanol, diethyl ether, tetrahydrofuran,4-methyl-2-pentanone, ethyl acetate, N,N-dimethylformamide,acetonitrile, water or a mixture of two or more of them in any ratio, inan excessive amount of the compound represented by the formula (XXIV) orin the presence of a base such as sodium hydroxide, potassium carbonate,sodium carbonate, sodium hydrogen carbonate, triethylamine orethyldiisopropylamine, within a temperature range of from 0° C. to therefluxing temperature of the reaction mixture for from 1 to 24 hours toobtain a compound represented by the formula (XIX) [wherein G², R² andR³ are the same as defined above, and R⁴ is a hydrogen atom, a C₁-C₆alkyl group or the like].

Some of the compounds represented by the formula (XXVII) are knowncompounds, and some of them are commercially available. The rest of themmay be synthesized, for example, by reaction scheme 12 or 13.

A compound represented by the formula (XXXI) [wherein Y¹, Y², Y³, Y⁴, Y⁵and J⁴ are the same as defined above] is reacted with silver nitrite inaccordance with a known method disclosed in the literature, for example,a method disclosed in J. Org. Chem., 2004, vol. 69, p. 6907, etc., ifnecessary in a solvent such as benzene, diethyl ether, tert-butyl methylether, acetonitrile, water or a mixture of two or more of them in anyratio, within a temperature range of from 0° C. to room temperature forfrom 30 minutes to 24 hours, or reacted with sodium nitrite-urea, forexample, in accordance with a method disclosed in Tetrahedron, 2009,vol. 65, p. 1660, etc., if necessary in a solvent such asN,N-dimethylformamide within a temperature range of from −78° C. to roomtemperature for from 1 to 6 hours, to obtain a compound represented bythe formula (XXVIIa) [wherein Y¹, Y², Y³, Y⁴ and Y⁵ are the same asdefined above] which is a compound of the formula (XXVII) wherein G² isG²-1.

The compounds represented by the formula (XXXI) used are knowncompounds, and some of them are commercially available. The rest of themcan be synthesized from known compounds in accordance with known methodsdisclosed in the literature.

A compound represented by the formula (XXXII) [wherein Y¹, Y², Y³, Y⁴and J⁴ are the same as defined above] and nitromethane are reacted inaccordance with a known method disclosed in the literature, for example,a method disclosed in Heterocycles, 1987, vol. 26, p. 3259,WO2004/096772, etc., if necessary in a solvent such as tetrahydrofuranor dimethylsulfoxide, if necessary in the presence of a base such assodium hydride or potassium tert-butoxide within a temperature range offrom 0 to 80° C. for from 1 to 24 hours to obtain a compound of theformula (XXVIIb) [wherein Y¹, Y², Y³ and Y⁴ are the same as definedabove] which is a compound of the formula (XXVII) wherein G² is G²-2.

The compounds represented by the formula (XXXII) used in this processare known compounds, and some of them are commercially available. Therest of them can be synthesized in accordance with known methodsdisclosed in the literature regarding known compounds.

In the respective reaction schemes, the compounds after a reaction canbe worked up by an ordinary procedure to obtain intermediates to bematerial compounds in processes A to D.

Further, the respective intermediates produced in such procedure may beused in the next step reaction without isolation nor purification.

As the oxime-substituted amide compounds of the present inventionrepresented by the formula (I) which can be produced by such processes,specifically, the following compounds of a first group and compounds ofa second group may, for example, be mentioned. However, the followingcompounds of a first group and compounds of a second group merelyexemplify the present invention, and the oxime-substituted amidecompounds of the present invention are by no means restricted thereto.

Further, combinations of substituents in the compounds of the aboverespective groups are shown in Tables 2 and 3. In the Tables, Et denotesethyl group, n-Pr and Pr-n denote normal propyl group, i-Pr and Pr-idenote isopropyl group, c-Pr and Pr-c denote cyclopropyl group, n-Bu andBu-n denote normal butyl group, i-Bu and Bu-i denote isobutyl group,s-Bu and Bu-s denote secondary butyl group, c-Bu and Bu-c denotecyclobutyl group, t-Bu and Bu-t denote tertiary butyl group, Pen denotespentyl group, c-Pen and Pen-c denote cyclopentyl group, Hex denoteshexyl group, c-Hex and Hex-c denote cyclohexyl group, Ph denotes phenylgroup, 1-Naph denotes 1-naphthyl group, and 2-Naph denotes 2-naphthylgroup.

Further, in Tables 2 and 3, aromatic heterocyclic rings represented byD-1-1a to D-35-b have the following structures, respectively.

For example, the expression “CH₂(D-5-3b)-3-Cl” means a3-chloroisoxazol-5-ylmethyl group.

In the Tables, aliphatic heterocyclic rings represented by E-2-1a toE-17-3a have the following structures, respectively.

For example, the expression “CH₂(E-4-1a)CHO” means a1-formylazetidin-2-ylmethyl group.

In the Tables, partial saturated heterocyclic rings represented by M-3-bto M-19-a have the following structures, respectively.

For example, the expression “CH₂(M-4-2a)CH₃” means a3-methyl-4,5-dihydroisoxazol-5-ylmethyl group.

Further, in the Tables, T-1 to T-9 have the following structures,respectively.

Compounds of First Group ([I]-1 to [I]-68)

Combinations of substituents in the compounds of the above first groupare shown in Table 2. In Table 2, the expression (R) or (S) in thecolumn substituent R² means that the proportion of the R isomer or the Sisomer is at least 90% in a mixture ratio of optical isomers due to thecarbon atom attached to R².

The expressions G²-1 to G²-10 in the column substituent G² mean thefollowing specific structures, respectively.

The expression “-” in the columns substituents Y², Y⁴ and Y⁵ means thatthere is no corresponding substituent present.

The expression (E) or (Z) in the column substituent R¹ means that theproportion of the E-isomer or the Z-isomer is at least 90% in a mixtureratio of oxime geometrical isomers attached to the substituent R¹.

TABLE 2 R² G² Y¹ Y² Y³ Y⁴ Y⁵ R¹ CH₃ G²-1 H H H H H CH₃ CH₃ G²-1 H H F HH CH₃ CH₃ G²-1 H H Cl H H CH₃ CH₃ G²-1 H H CH₃ H H CH₃ CH₃ G²-1 H H Et HH CH₃ CH₃ G²-1 H H i-Pr H H CH₃ CH₃ G²-1 H H c-Hex H H CH₃ CH₃ G²-1 H HOCHF₂ H H CH₃ CH₃ G²-1 H H NO₂ H H CH₃ CH₃ G²-1 H H CN H H CH₃ CH₃ G²-1H F F H H CH₃ CH₃ G²-1 H F Cl H H CH₃ CH₃ G²-1 H Cl H H H CH₃ CH₃ G²-1 HCl H Cl H CH₃ CH₃ G²-1 H Cl F H H CH₃ CH₃ G²-1 H Cl Br H H CH₃ CH₃ G²-1H Cl CH₃ H H CH₃ CH₃ G²-1 H Cl CH₃ CH₃ H CH₃ CH₃ G²-1 H Br H H H CH₃ CH₃G²-1 H Br Cl H H CH₃ CH₃ G²-1 H Br Br H H CH₃ CH₃ G²-1 H Br OCF₃ H H CH₃CH₃ G²-1 H CH₃ H H H CH₃ CH₃ G²-1 H CH₃ Cl H H CH₃ CH₃ G²-1 H CH₃ Br H HCH₃ CH₃ G²-1 H CH₃ CH₃ H H CH₃ CH₃ G²-1 H CH₃ OCH₃ H H CH₃ CH₃ G²-1 HCH₃ OCF₃ H H CH₃ CH₃ G²-1 H CF₃ H H H CH₃ CH₃ G²-1 H CF₃ Cl H H CH₃ CH₃G²-1 H OCH₃ H H H CH₃ CH₃ G²-1 H OCH₃ Cl H H CH₃ CH₃ G²-1 H OCHF₂ H H HCH₃ CH₃ G²-1 H OCF₃ H H H CH₃ CH₃ G²-1 H OPh H H H CH₃ CH₃ G²-1 H OPh FH H CH₃ CH₃ G²-1 H —OCH₂O— H H CH₃ CH₃ G²-1 H —OCF₂O— H H CH₃ CH₃ G²-1 H—OCF₂CF₂O— H H CH₃ CH₃ G²-1 H —CH═CHC(CH₃)═CH— H H CH₃ CH₃ G²-1 F H H HH CH₃ CH₃ G²-1 F H H H F CH₃ CH₃ G²-1 F H F H H CH₃ CH₃ G²-1 F H F H FCH₃ CH₃ G²-1 F H F F H CH₃ CH₃ G²-1 F H Cl H H CH₃ CH₃ G²-1 F H Cl H HCH₃(E) CH₃ G²-1 F H Cl H H CH₃(Z) CH₃(S) G²-1 F H Cl H H CH₃ CH₃(S) G²-1F H Cl H H CH₃(E) CH₃(S) G²-1 F H Cl H H CH₃(Z) CH₃ G²-1 F H Cl F H CH₃CH₃ G²-1 F H Cl Cl H CH₃ CH₃ G²-1 F H Br H H CH₃ CH₃ G²-1 F H Br F H CH₃CH₃ G²-1 Cl H H H H CH₃ CH₃ G²-1 Cl H H H F CH₃ CH₃ G²-1 Cl H H H Cl CH₃H G²-1 Cl H F H H CH₃ CH₃ G²-1 Cl H F H H CH₃ CH₃ G²-1 Cl H F H H CH₃(E)CH₃ G²-1 Cl H F H H CH₃(Z) CH₃(S) G²-1 Cl H F H H CH₃ CH₃(S) G²-1 Cl H FH H CH₃(E) CH₃(S) G²-1 Cl H F H H CH₃(Z) CH₃ G²-1 Cl H F F H CH₃ H G²-1Cl H Cl H H CH₃ H G²-1 Cl H Cl H H CH₃(Z) CH₃ G²-1 Cl H Cl H H CH₃ CH₃G²-1 Cl H Cl H H CH₃(E) CH₃ G²-1 Cl H Cl H H CH₃(Z) CH₃(R) G²-1 Cl H ClH H CH₃ CH₃(R) G²-1 Cl H Cl H H CH₃(E) CH₃(R) G²-1 Cl H Cl H H CH₃(Z)CH₃(S) G²-1 Cl H Cl H H CH₃ CH₃(S) G²-1 Cl H Cl H H CH₃(E) CH₃(S) G²-1Cl H Cl H H CH₃(Z) CH₃ G²-1 Cl H Cl H Cl CH₃ CH₃ G²-1 Cl H Cl F H CH₃CH₃ G²-1 Cl H Cl Cl H CH₃ CH₃ G²-1 Cl H Br H H CH₃ CH₃ G²-1 Cl H Br H HCH₃(E) CH₃(S) G²-1 Cl H Br H H CH₃ CH₃(S) G²-1 Cl H Br H H CH₃(E) CH₃G²-1 Cl H Br H Cl CH₃ CH₃ G²-1 Cl H I H Cl CH₃ CH₃ G²-1 Cl H CH₃ H H CH₃CH₃ G²-1 Cl H CH₃ H H CH₃(E) CH₃(S) G²-1 Cl H CH₃ H H CH₃ CH₃(S) G²-1 ClH CH₃ H H CH₃(E) CH₃ G²-1 Cl H CH₃ H Cl CH₃ CH₃ G²-1 Cl H CF₃ H H CH₃CH₃ G²-1 Cl H CF₃ H H CH₃(E) CH₃(S) G²-1 Cl H CF₃ H H CH₃ CH₃(S) G²-1 ClH CF₃ H H CH₃(E) CH₃ G²-1 Cl H CF₃ H Cl CH₃ CH₃ G²-1 Cl H OCH₃ H H CH₃CH₃ G²-1 Cl H OCH₃ H Cl CH₃ CH₃ G²-1 Cl H OCHF₂ H H CH₃ CH₃ G²-1 Cl HOCH₂CH═CCl₂ H H CH₃ CH₃ G²-1 Cl H OPh H H CH₃ CH₃ G²-1 Cl H O(Ph-3-F) HH CH₃ CH₃ G²-1 Cl H O(Ph-4-F) H H CH₃ CH₃ G²-1 Cl H SCH₃ H H CH₃ CH₃G²-1 Cl H S(O)CH₃ H H CH₃ CH₃ G²-1 Cl H SO₂CH₃ H H CH₃ CH₃ G²-1 Cl HSCF₃ H H CH₃ CH₃ G²-1 Cl H CH═NOCH₃ H H CH₃ CH₃ G²-1 Cl H CH═NOEt H HCH₃ CH₃ G²-1 Cl H C(CH₃)═NOCH₃ H H CH₃ CH₃ G²-1 Cl H C(CH₃)═NOEt H H CH₃CH₃ G²-1 Cl H C(Et)═NOCH₃ H H CH₃ CH₃ G²-1 Cl H C(Et)═NOEt H H CH₃ CH₃G²-1 Cl H CN H H CH₃ CH₃ G²-1 Cl H C(O)NH₂ H H CH₃ CH₃ G²-1 Cl H C(S)NH₂H H CH₃ CH₃ G²-1 Cl H CH═CH₂ H H CH₃ CH₃ G²-1 Cl H C≡CH H H CH₃ CH₃ G²-1Cl H C≡CH H H CH₃(E) CH₃(S) G²-1 Cl H C≡CH H H CH₃ CH₃(S) G²-1 Cl H C≡CHH H CH₃(E) CH₃ G²-1 Cl H C≡CCH₃ H H CH₃ CH₃ G²-1 Cl H C≡CCH₃ H H CH₃(E)CH₃ G²-1 Cl H C≡CEt H H CH₃ CH₃ G²-1 Cl H C≡CPr-n H H CH₃ CH₃ G²-1 Cl HC≡CPr-c H H CH₃ CH₃ G²-1 Cl H C≡CPr-c H H CH₃(E) CH₃ G²-1 Cl H C≡CBu-n HH CH₃ CH₃ G²-1 Cl H C≡CBu-t H H CH₃ CH₃ G²-1 Cl H C≡CBu-t H H CH₃(E)CH₃(S) G²-1 Cl H C≡CBu-t H H CH₃ CH₃(S) G²-1 Cl H C≡CBu-t H H CH₃(E) CH₃G²-1 Cl H C≡CPen-c H H CH₃ CH₃ G²-1 Cl H C≡CPen-c H H CH₃(E) CH₃ G²-1 ClH C≡CCl H H CH₃ CH₃ G²-1 Cl H C≡CBr H H CH₃ CH₃ G²-1 Cl H C≡CI H H CH₃CH₃ G²-1 Cl H C≡CC(CH₃)₂OH H H CH₃ CH₃ G²-1 Cl H C≡CC(CH₃)₂OH H H CH₃(E)CH₃ G²-1 Cl H C≡CC(CH₃)₂OCH₃ H H CH₃ CH₃ G²-1 Cl H C≡CC(CH₃)₂OCH₃ H HCH₃(E) CH₃ G²-1 Cl H C≡CSi(CH₃)₃ H H CH₃ CH₃ G²-1 Cl H C≡CSi(CH₃)₃ H HCH₃(E) CH₃(S) G²-1 Cl H C≡CSi(CH₃)₃ H H CH₃ CH₃(S) G²-1 Cl H C≡CSi(CH₃)₃H H CH₃(E) CH₃ G²-1 Cl H C≡CPh H H CH₃ CH₃ G²-1 Cl H C≡CPh H H CH₃(E)CH₃(S) G²-1 Cl H C≡CPh H H CH₃ CH₃(S) G²-1 Cl H C≡CPh H H CH₃(E) CH₃G²-1 Cl H Ph H H CH₃ CH₃ G²-1 Cl H Ph-4-OCF₃ H H CH₃ CH₃ G²-1 Cl H—OCH₂O— H CH₃ CH₃ G²-1 Cl Cl H H H CH₃ CH₃ G²-1 Cl Cl H H Cl CH₃ CH₃G²-1 Cl Cl Cl H H CH₃ CH₃ G²-1 Cl —OCF₂O— H H CH₃ CH₃ G²-1 Br H H OCH₃ HCH₃ CH₃ G²-1 Br H F H H CH₃ CH₃ G²-1 Br H F F H CH₃ CH₃ G²-1 Br H Cl HBr CH₃ CH₃ G²-1 Br H I H Br CH₃ CH₃ G²-1 Br H Et H Br CH₃ CH₃ G²-1 Br HCF₃ H H CH₃ CH₃ G²-1 Br H CF₃ H Br CH₃ CH₃ G²-1 CH₃ H H H H CH₃ CH₃ G²-1CH₃ H H H Cl CH₃ CH₃ G²-1 CH₃ H H H CH₃ CH₃ CH₃ G²-1 CH₃ H H CH₃ H CH₃CH₃ G²-1 CH₃ H F H H CH₃ CH₃ G²-1 CH₃ H Cl H Cl CH₃ CH₃ G²-1 CH₃ H Br HH CH₃ CH₃ G²-1 CH₃ H CH₃ H Cl CH₃ CH₃ G²-1 CH₃ H CH₃ H CH₃ CH₃ CH₃ G²-1CH₃ H CF₃ H H CH₃ CH₃ G²-1 CH₃ H OCH₃ H H CH₃ CH₃ G²-1 CH₃ H OPr-i H HCH₃ CH₃ G²-1 CH₃ H OCHF₂ H H CH₃ CH₃ G²-1 CH₃ H —OCH₂O— H CH₃ CH₃ G²-1CH₃ H —OCF₂O— H CH₃ CH₃ G²-1 CH₃ Cl H H H CH₃ CH₃ G²-1 CH₃ Cl Cl H H CH₃CH₃ G²-1 CH₃ CH₃ Cl H H CH₃ CH₃ G²-1 CH₃ —OCH₂O— H H CH₃ CH₃ G²-1 CH₃—OCF₂O— H H CH₃ CH₃ G²-1 CH₃ —OCF₂CF₂O— H H CH₃ CH₃ G²-1 CF₃ H H H H CH₃CH₃ G²-1 CF₃ H H H Cl CH₃ CH₃ G²-1 CF₃ H CF₃ H H CH₃ CH₃ G²-1 CH₂OCH₃ HH H H CH₃ CH₃ G²-1 OCH₃ H H H H CH₃ CH₃ G²-1 OCH₃ H H Br H CH₃ CH₃ G²-1OCH₃ H H OCH₃ H CH₃ CH₃ G²-1 OCH₃ OCH₃ H H H CH₃ CH₃ G²-1 OPh H H H HCH₃ CH₃ G²-1 —OCH₂O— H H H CH₃ CH₃ G²-1 —OCF₂O— H H H CH₃ H G²-2 H H CF₃H — CH₃ H G²-2 F H Cl H — CH₃ H G²-2 F H Cl H — CH₃(Z) CH₃ G²-2 F H Cl H— CH₃(Z) CH₃(S) G²-2 F H Cl H — CH₃(Z) H G²-2 F H Br H — CH₃ H G²-2 F HBr H — CH₃(Z) CH₃ G²-2 F H Br H — CH₃(Z) CH₃(S) G²-2 F H Br H — CH₃(Z) HG²-2 F H CF₃ H — CH₃ H G²-2 F H CF₃ H — CH₃(Z) H G²-2 Cl H H H — CH₃(Z)H G²-2 Cl H F H — CH₃ H G²-2 Cl H F H — CH₃(Z) CH₃ G²-2 Cl H F H —CH₃(Z) CH₃(S) G²-2 Cl H F H — CH₃(Z) H G²-2 Cl H Cl H — CH₃ H G²-2 Cl HCl H — CH₃(E) H G²-2 Cl H Cl H — CH₃(Z) CH₃ G²-2 Cl H Cl H — CH₃ CH₃G²-2 Cl H Cl H — CH₃(E) CH₃ G²-2 Cl H Cl H — CH₃(Z) CH₃(R) G²-2 Cl H ClH — CH₃ CH₃(R) G²-2 Cl H Cl H — CH₃(E) CH₃(R) G²-2 Cl H Cl H — CH₃(Z)CH₃(S) G²-2 Cl H Cl H — CH₃ CH₃(S) G²-2 Cl H Cl H — CH₃(E) CH₃(S) G²-2Cl H Cl H — CH₃(Z) Et G²-2 Cl H Cl H — CH₃ n-Pr G²-2 Cl H Cl H — CH₃i-Pr G²-2 Cl H Cl H — CH₃ c-Pr G²-2 Cl H Cl H — CH₃ CH₂F G²-2 Cl H Cl H— CH₃ CF₃ G²-2 Cl H Cl H — CH₃ CH₂OCH₃ G²-2 Cl H Cl H — CH₃ CH₂SCH₃ G²-2Cl H Cl H — CH₃ Ph G²-2 Cl H Cl H — CH₃(Z) H G²-2 Cl H Cl F — CH₃ H G²-2Cl H Cl F — CH₃(Z) CH₃ G²-2 Cl H Cl F — CH₃ CH₃ G²-2 Cl H Cl F — CH₃(Z)CH₃(S) G²-2 Cl H Cl F — CH₃ CH₃(S) G²-2 Cl H Cl F — CH₃(Z) H G²-2 Cl HCl Cl — CH₃ H G²-2 Cl H Cl Cl — CH₃(Z) H G²-2 Cl H Br H — CH₃ H G²-2 ClH Br H — CH₃(E) H G²-2 Cl H Br H — CH₃(Z) CH₃ G²-2 Cl H Br H — CH₃ CH₃G²-2 Cl H Br H — CH₃(Z) CH₃(S) G²-2 Cl H Br H — CH₃ CH₃(S) G²-2 Cl H BrH — CH₃(Z) H G²-2 Cl H CF₃ H — CH₃ H G²-2 Cl H CF₃ H — CH₃(Z) CH₃ G²-2Cl H CF₃ H — CH₃ CH₃ G²-2 Cl H CF₃ H — CH₃(Z) CH₃(R) G²-2 Cl H CF₃ H —CH₃ CH₃(R) G²-2 Cl H CF₃ H — CH₃(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₃ CH₃(S)G²-2 Cl H CF₃ H — CH₃(Z) H G²-2 Cl H OCH₃ H — CH₃ H G²-2 Cl H OCHF₂ H —CH₃ H G²-2 Cl H OCF₃ H — CH₃ H G²-2 Cl H O(Ph-4-Cl) H — CH₃ H G²-2 Cl HCH═NOCH₃ H — CH₃ H G²-2 Cl H CH═NOEt H — CH₃ H G²-2 Cl H C(CH₃)═NOCH₃ H— CH₃ CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H — CH₃ CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H— CH₃ H G²-2 Cl H C(CH₃)═NOEt H — CH₃ H G²-2 Cl H C(Et)═NOCH₃ H — CH₃ HG²-2 Cl H C≡CH H — CH₃ H G²-2 Cl H C≡CH H — CH₃(Z) H G²-2 Cl H C≡CCH₃ H— CH₃ H G²-2 Cl H C≡CCH₃ H — CH₃(Z) H G²-2 Cl H C≡CEt H — CH₃ H G²-2 ClH C≡CPr-n H — CH₃ H G²-2 Cl H C≡CPr-c H — CH₃ H G²-2 Cl H C≡CPr-c H —CH₃(Z) CH₃ G²-2 Cl H C≡CPr-c H — CH₃ CH₃ G²-2 Cl H C≡CPr-c H — CH₃(Z)CH₃(S) G²-2 Cl H C≡CPr-c H — CH₃ CH₃(S) G²-2 Cl H C≡CPr-c H — CH₃(Z) HG²-2 Cl H C≡CBu-n H — CH₃ H G²-2 Cl H C≡CBu-t H — CH₃ H G²-2 Cl HC≡CBu-t H — CH₃(Z) CH₃ G²-2 Cl H C≡CBu-t H — CH₃ CH₃ G²-2 Cl H C≡CBu-t H— CH₃(Z) CH₃(S) G²-2 Cl H C≡CBu-t H — CH₃ CH₃(S) G²-2 Cl H C≡CBu-t H —CH₃(Z) H G²-2 Cl H C≡CPen-c H — CH₃ H G²-2 Cl H C≡CPen-c H — CH₃(Z) HG²-2 Cl H C≡CCl H — CH₃ H G²-2 Cl H C≡CBr H — CH₃ H G²-2 Cl H C≡CI H —CH₃ H G²-2 Cl H C≡CC(CH₃)₂OH H — CH₃ H G²-2 Cl H C≡CC(CH₃)₂OH H — CH₃(Z)H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₃ H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₃(Z)H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₃ H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₃(Z) HG²-2 Cl H C≡CPh H — CH₃ H G²-2 Cl H C≡CPh H — CH₃(Z) H G²-2 Cl F Cl H —CH₃ H G²-2 Cl F Cl H — CH₃(Z) CH₃ G²-2 Cl F Cl H — CH₃(Z) CH₃(S) G²-2 ClF Cl H — CH₃(Z) H G²-2 Cl Cl Cl H — CH₃ H G²-2 Cl Cl Cl H — CH₃(Z) CH₃G²-2 Cl Cl Cl H — CH₃(Z) CH₃(S) G²-2 Cl Cl Cl H — CH₃(Z) H G²-2 Br H F H— CH₃ H G²-2 Br H F H — CH₃(Z) H G²-2 Br H Cl H — CH₃ H G²-2 Br H Cl H —CH₃(Z) CH₃ G²-2 Br H Cl H — CH₃(Z) CH₃(S) G²-2 Br H Cl H — CH₃(Z) H G²-2Br H Br H — CH₃ H G²-2 Br H Br H — CH₃(Z) CH₃ G²-2 Br H Br H — CH₃ CH₃G²-2 Br H Br H — CH₃(Z) CH₃(S) G²-2 Br H Br H — CH₃ CH₃(S) G²-2 Br H BrH — CH₃(Z) H G²-2 Br H CF₃ H — CH₃ H G²-2 Br H CF₃ H — CH₃(Z) H G²-2OCH₃ H Cl H — CH₃ H G²-3 Cl — Cl H H CH₃ CH₃ G²-3 Cl — Cl H H CH₃ H G²-4Cl H Cl — H CH₃ CH₃ G²-4 Cl H Cl — H CH₃ H G²-4 Cl H CF₃ — H CH₃ H G²-4Cl H C≡CPr-c — H CH₃ CH₃ G²-4 Cl H C≡CPr-c — H CH₃ H G²-4 Cl H C≡CBu-t —H CH₃ CH₃ G²-4 Cl H C≡CBu-t — H CH₃ H G²-6 Cl — Cl H — CH₃ CH₃ G²-6 Cl —Cl H — CH₃ H G²-7 Cl H Br — — CH₃ CH₃ G²-7 Cl H Br — — CH₃ H G²-7 Cl HC≡CPr-c — — CH₃ CH₃ G²-7 Cl H C≡CPr-c — — CH₃ H G²-7 Cl H C≡CBu-t — —CH₃ CH₃ G²-7 Cl H C≡CBu-t — — CH₃ H G²-7 Cl Cl Cl — — CH₃ CH₃ G²-8 CH₃ —CH₃ H — CH₃ H G²-9 F H Br — — CH₃ CH₃ G²-9 Cl H Cl — — CH₃ CH₃ G²-9 Cl HCl — — CH₃(Z) CH₃(S) G²-9 Cl H Cl — — CH₃ CH₃(S) G²-9 Cl H Cl — — CH₃(Z)H G²-9 Cl H Br — — CH₃ CH₃ G²-9 Cl H Br — — CH₃ CH₃ G²-9 Cl H Br — —CH₃(Z) CH₃(S) G²-9 Cl H Br — — CH₃ CH₃(S) G²-9 Cl H Br — — CH₃(Z) CH₃G²-9 Cl H C≡CH — — CH₃ CH₃ G²-9 Cl H C≡CH — — CH₃(Z) CH₃(S) G²-9 Cl HC≡CH — — CH₃ CH₃(S) G²-9 Cl H C≡CH — — CH₃(Z) CH₃ G²-9 Cl H C≡CCH₃ — —CH₃ CH₃ G²-9 Cl H C≡CCH₃ — — CH₃(Z) CH₃ G²-9 Cl H C≡CEt — — CH₃ CH₃ G²-9Cl H C≡CPr-n — — CH₃ CH₃ G²-9 Cl H C≡CPr-c — — CH₃ CH₃ G²-9 Cl H C≡CPr-c— — CH₃(Z) CH₃ G²-9 Cl H C≡CBu-n — — CH₃ CH₃ G²-9 Cl H C≡CBu-t — — CH₃CH₃ G²-9 Cl H C≡CBu-t — — CH₃(Z) CH₃(S) G²-9 Cl H C≡CBu-t — — CH₃ CH₃(S)G²-9 Cl H C≡CBu-t — — CH₃(Z) CH₃ G²-9 Cl H C≡CPen-c — — CH₃ CH₃ G²-9 ClH C≡CPen-c — — CH₃(Z) CH₃ G²-9 Cl H C≡CCl — — CH₃ CH₃ G²-9 Cl H C≡CBr —— CH₃ CH₃ G²-9 Cl H C≡CI — — CH₃ CH₃ G²-9 Cl H C≡CC(CH₃)₂OH — — CH₃ CH₃G²-9 Cl H C≡CC(CH₃)₂OH — — CH₃(Z) CH₃ G²-9 Cl H C≡CC(CH₃)₂OCH₃ — — CH₃CH₃ G²-9 Cl H C≡CC(CH₃)₂OCH₃ — — CH₃(Z) CH₃ G²-9 Cl H C≡CSi(CH₃)₃ — —CH₃ CH₃ G²-9 Cl H C≡CSi(CH₃)₃ — — CH₃(Z) CH₃(S) G²-9 Cl H C≡CSi(CH₃)₃ —— CH₃ CH₃(S) G²-9 Cl H C≡CSi(CH₃)₃ — — CH₃(Z) CH₃ G²-9 Cl H C≡CPh — —CH₃ CH₃ G²-9 Cl H C≡CPh — — CH₃(Z) CH₃(S) G²-9 Cl H C≡CPh — — CH₃ CH₃(S)G²-9 Cl H C≡CPh — — CH₃(Z) H G²-9 Cl Cl Cl — — CH₃ CH₃ G²-9 Cl Cl Cl — —CH₃ CH₃ G²-9 Cl Cl Cl — — CH₃(Z) CH₃(S) G²-9 Cl Cl Cl — — CH₃ CH₃(S)G²-9 Cl Cl Cl — — CH₃(Z) CH₃ G²-9 Cl —CH═CHCCl═CH— — — CH₃ CH₃ G²-9 Cl—CH═CClCH═CH— — — CH₃ CH₃ G²-9 Cl —CH═CBrCH═CH— — — CH₃ H G²-9 Br H Br —— CH₃ H G²-9 Br Br Br — — CH₃ H G²-9 Br CH₃ Br — — CH₃ H G²-9 CH₃ H Cl —— CH₃ H G²-9 CH₃ H Br — — CH₃ H G²-9 CH₃ Br Br — — CH₃ CH₃ G²-10 H — ClCl — CH₃ CH₃ G²-10 H — *—CH═CHCH═CH— — CH₃ H G²-10 Cl — Cl H — CH₃ CH₃G²-10 Cl — Cl H — CH₃ CH₃ G²-10 Cl — Cl Cl — CH₃ CH₃ G²-10 Br — Cl Cl —CH₃ H G²-10 Br — Br H — CH₃ CH₃ G²-10 Br — Br H — CH₃ H G²-10 CH₃ — Cl H— CH₃ CH₃ G²-10 CH₃ — Cl H — CH₃ H G²-10 CH₃ — Br H — CH₃ CH₃ G²-10 CH₃— CH₃ H — CH₃ CH₃ G²-1 H H Br H H Et CH₃ G²-1 H H I H H Et CH₃ G²-1 H Ht-Bu H H Et CH₃ G²-1 H H CF₃ H H Et CH₃ G²-1 H H OCF₃ H H Et CH₃ G²-1 HH OPh H H Et CH₃ G²-1 H H Ph H H Et CH₃ G²-1 H F F F H Et CH₃ G²-1 H ClCl H H Et CH₃ G²-1 H Br H CF₃ H Et CH₃ G²-1 H OPr-i H H H Et CH₃ G²-1 H—CH═CHCH═CH— H H Et CH₃ G²-1 F H F H H Et CH₃ G²-1 F H Cl H H Et CH₃G²-1 F H Cl H H Et(E) CH₃(S) G²-1 F H Cl H H Et CH₃(S) G²-1 F H Cl H HEt(E) CH₃ G²-1 F H Br H H Et CH₃ G²-1 F H Br F H Et CH₃ G²-1 F H CF₃ H HEt CH₃ G²-1 Cl H H F H Et CH₃ G²-1 Cl H H Cl H Et CH₃ G²-1 Cl H H CF₃ HEt CH₃ G²-1 Cl H F H H Et CH₃ G²-1 Cl H F H H Et(E) CH₃(S) G²-1 Cl H F HH Et CH₃(S) G²-1 Cl H F H H Et(E) CH₃ G²-1 Cl H Cl H H Et CH₃ G²-1 Cl HCl H H Et(E) CH₃(S) G²-1 Cl H Cl H H Et CH₃(S) G²-1 Cl H Cl H H Et(E)CH₃ G²-1 Cl H Br H H Et CH₃ G²-1 Cl H CH₃ H H Et CH₃ G²-1 Cl H CH₃ H HEt(E) CH₃(S) G²-1 Cl H CH₃ H H Et CH₃(S) G²-1 Cl H CH₃ H H Et(E) CH₃G²-1 Cl H CF₃ H H Et CH₃ G²-1 Cl H OCH₃ H H Et CH₃ G²-1 Cl H SCH₃ H H EtCH₃ G²-1 Cl H S(O)CH₃ H H Et CH₃ G²-1 Cl H SO₂CH₃ H H Et CH₃ G²-1 Cl HC(O)CH₃ H H Et CH₃ G²-1 Cl H C(CH₃)═NOCH₃ H H Et CH₃ G²-1 Cl H CN H H EtCH₃ G²-1 Cl H (M-7-b)-4,4-(CH₃)₂ H H Et CH₃ G²-1 Cl H CH═CH₂ H H Et CH₃G²-1 Cl H Ph H H Et CH₃ G²-1 Cl H Ph-4-OCF₃ H H Et CH₃ G²-1 Cl H D-3-a HH Et CH₃ G²-1 Cl H D-7-a H H Et CH₃ G²-1 Cl H (D-7-b)-3-CF₃ H H Et CH₃G²-1 Cl F H H H Et CH₃ G²-1 Br H F H H Et CH₃ G²-1 Br H F F H Et CH₃G²-1 CH₃ H Cl H H Et CH₃ G²-1 CH₃ H CH₃ H H Et CH₃ G²-1 CF₃ H Cl H H EtCH₃ G²-1 OCH₃ H Cl H H Et CH₃ G²-1 CH═NOEt H Cl H H Et CH₃ G²-1 E-9-1a HCl H H Et CH₃ G²-1 —CH═CHCH═CH— Br H H Et H G²-2 F H Cl H — Et H G²-2 FH Cl H — Et(Z) CH₃ G²-2 F H Cl H — Et(Z) CH₃(S) G²-2 F H Cl H — Et(Z) HG²-2 F H Br H — Et H G²-2 F H Br H — Et(Z) CH₃ G²-2 F H Br H — Et(Z)CH₃(S) G²-2 F H Br H — Et(Z) H G²-2 F H CF₃ H — Et H G²-2 F H CF₃ H —Et(Z) H G²-2 Cl H F H — Et H G²-2 Cl H F H — Et(Z) CH₃ G²-2 Cl H F H —Et(Z) CH₃(S) G²-2 Cl H F H — Et(Z) H G²-2 Cl H Cl H — Et H G²-2 Cl H ClH — Et(E) H G²-2 Cl H Cl H — Et(Z) CH₃ G²-2 Cl H Cl H — Et CH₃ G²-2 Cl HCl H — Et(E) CH₃ G²-2 Cl H Cl H — Et(Z) CH₃(S) G²-2 Cl H Cl H — EtCH₃(S) G²-2 Cl H Cl H — Et(E) CH₃(S) G²-2 Cl H Cl H — Et(Z) H G²-2 Cl HCl F — Et H G²-2 Cl H Cl F — Et(E) H G²-2 Cl H Cl F — Et(Z) CH₃ G²-2 ClH Cl F — Et CH₃ G²-2 Cl H Cl F — Et(Z) CH₃(S) G²-2 Cl H Cl F — Et CH₃(S)G²-2 Cl H Cl F — Et(Z) t-Bu G²-2 Cl H Cl H — Et H G²-2 Cl H Cl Cl — Et HG²-2 Cl H Cl Cl — Et(Z) H G²-2 Cl H Br H — Et H G²-2 Cl H Br H — Et(E) HG²-2 Cl H Br H — Et(Z) CH₃ G²-2 Cl H Br H — Et CH₃ G²-2 Cl H Br H —Et(Z) CH₃(S) G²-2 Cl H Br H — Et CH₃(S) G²-2 Cl H Br H — Et(Z) H G²-2 ClH CF₃ H — Et H G²-2 Cl H CF₃ H — Et(E) H G²-2 Cl H CF₃ H — Et(Z) CH₃G²-2 Cl H CF₃ H — Et CH₃ G²-2 Cl H CF₃ H — Et(Z) CH₃(S) G²-2 Cl H CF₃ H— Et CH₃(S) G²-2 Cl H CF₃ H — Et(Z) H G²-2 Cl H CH═NOCH₃ H — Et H G²-2Cl H CH═NOEt H — Et H G²-2 Cl H C(CH₃)═NOCH₃ H — Et CH₃ G²-2 Cl HC(CH₃)═NOCH₃ H — Et CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — Et H G²-2 Cl HC(CH₃)═NOEt H — Et H G²-2 Cl H C(Et)═NOCH₃ H — Et H G²-2 Cl H C≡CH H —Et H G²-2 Cl H C≡CH H — Et(Z) H G²-2 Cl H C≡CCH₃ H — Et H G²-2 Cl HC≡CCH₃ H — Et(Z) H G²-2 Cl H C≡CEt H — Et H G²-2 Cl H C≡CPr-n H — Et HG²-2 Cl H C≡CPr-c H — Et H G²-2 Cl H C≡CPr-c H — Et(Z) CH₃ G²-2 Cl HC≡CPr-c H — Et CH₃ G²-2 Cl H C≡CPr-c H — Et(Z) CH₃(S) G²-2 Cl H C≡CPr-cH — Et CH₃(S) G²-2 Cl H C≡CPr-c H — Et(Z) H G²-2 Cl H C≡CBu-n H — Et HG²-2 Cl H C≡CBu-t H — Et H G²-2 Cl H C≡CBu-t H — Et(Z) CH₃ G²-2 Cl HC≡CBu-t H — Et CH₃ G²-2 Cl H C≡CBu-t H — Et(Z) CH₃(S) G²-2 Cl H C≡CBu-tH — Et CH₃(S) G²-2 Cl H C≡CBu-t H — Et(Z) H G²-2 Cl H C≡CPen-c H — Et HG²-2 Cl H C≡CPen-c H — Et(Z) H G²-2 Cl H C≡CCl H — Et H G²-2 Cl H C≡CBrH — Et H G²-2 Cl H C≡CI H — Et H G²-2 Cl H C≡CC(CH₃)₂OH H — Et H G²-2 ClH C≡CC(CH₃)₂OH H — Et(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — Et H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — Et(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — Et H G²-2 Cl HC≡CSi(CH₃)₃ H — Et(Z) H G²-2 Cl H C≡CPh H — Et H G²-2 Cl H C≡CPh H —Et(Z) H G²-2 Cl H CN H — Et H G²-2 Cl F Cl H — Et H G²-2 Cl F Cl H —Et(Z) CH₃ G²-2 Cl F Cl H — Et(Z) CH₃(S) G²-2 Cl F Cl H — Et(Z) H G²-2 ClCl Cl H — Et H G²-2 Cl Cl Cl H — Et(Z) CH₃ G²-2 Cl Cl Cl H — Et(Z)CH₃(S) G²-2 Cl Cl Cl H — Et(Z) H G²-2 Br H F H — Et H G²-2 Br H F H —Et(Z) H G²-2 Br H Cl H — Et H G²-2 Br H Cl H — Et(Z) CH₃ G²-2 Br H Cl H— Et(Z) CH₃(S) G²-2 Br H Cl H — Et(Z) H G²-2 Br H Br H — Et H G²-2 Br HBr H — Et(Z) CH₃ G²-2 Br H Br H — Et CH₃ G²-2 Br H Br H — Et(Z) CH₃(S)G²-2 Br H Br H — Et CH₃(S) G²-2 Br H Br H — Et(Z) H G²-2 Br H CF₃ H — EtH G²-2 Br H CF₃ H — Et(Z) H G²-3 Cl — H Cl H Et H G²-4 Cl H Cl — H EtCH₃ G²-4 Cl H Cl — H Et H G²-4 Cl H CF₃ — H Et H G²-6 Cl — Cl H — Et CH₃G²-6 Cl — Cl H — Et H G²-7 Cl H Br — — Et CH₃ G²-7 Cl H Br — — Et H G²-7Cl Cl Cl — — Et CH₃ G²-9 Cl H Cl — — Et CH₃ G²-9 Cl H Cl — — Et(Z) CH₃G²-9 Cl H Br — — Et CH₃ G²-9 Cl H Br — — Et(Z) CH₃ G²-9 Cl H C≡CPr-c — —Et CH₃ G²-9 Cl H C≡CPr-c — — Et(Z) CH₃ G²-9 Cl H C≡CBu-t — — Et CH₃ G²-9Cl H C≡CBu-t — — Et(Z) H G²-9 Cl Cl Cl — — Et CH₃ G²-9 Cl Cl Cl — — EtCH₃ G²-9 Cl Cl Cl — — Et(Z) CH₃ G²-10 Cl — H H — Et CH₃ G²-10 Cl — Cl H— Et CH₃ G²-1 Cl H F H H n-Pr CH₃ G²-1 Cl H F H H n-Pr(E) CH₃(S) G²-1 ClH F H H n-Pr CH₃(S) G²-1 Cl H F H H n-Pr(E) H G²-2 F H Cl H — n-Pr HG²-2 F H Cl H — n-Pr(Z) CH₃ G²-2 F H Cl H — n-Pr(Z) CH₃(S) G²-2 F H Cl H— n-Pr(Z) H G²-2 F H Br H — n-Pr H G²-2 F H Br H — n-Pr(Z) CH₃ G²-2 F HBr H — n-Pr(Z) CH₃(S) G²-2 F H Br H — n-Pr(Z) H G²-2 F H CF₃ H — n-Pr HG²-2 F H CF₃ H — n-Pr(Z) H G²-2 Cl H F H — n-Pr H G²-2 Cl H F H —n-Pr(Z) CH₃ G²-2 Cl H F H — n-Pr(Z) CH₃(S) G²-2 Cl H F H — n-Pr(Z) HG²-2 Cl H Cl H — n-Pr H G²-2 Cl H Cl H — n-Pr(Z) CH₃ G²-2 Cl H Cl H —n-Pr CH₃ G²-2 Cl H Cl H — n-Pr(Z) CH₃(S) G²-2 Cl H Cl H — n-Pr CH₃(S)G²-2 Cl H Cl H — n-Pr(Z) H G²-2 Cl H Cl F — n-Pr H G²-2 Cl H Cl F —n-Pr(Z) CH₃ G²-2 Cl H Cl F — n-Pr CH₃ G²-2 Cl H Cl F — n-Pr(Z) CH₃(S)G²-2 Cl H Cl F — n-Pr CH₃(S) G²-2 Cl H Cl F — n-Pr(Z) H G²-2 Cl H Cl Cl— n-Pr H G²-2 Cl H Cl Cl — n-Pr(Z) H G²-2 Cl H Br H — n-Pr H G²-2 Cl HBr H — n-Pr(Z) CH₃ G²-2 Cl H Br H — n-Pr CH₃ G²-2 Cl H Br H — n-Pr(Z)CH₃(S) G²-2 Cl H Br H — n-Pr CH₃(S) G²-2 Cl H Br H — n-Pr(Z) H G²-2 Cl HCF₃ H — n-Pr H G²-2 Cl H CF₃ H — n-Pr(E) H G²-2 Cl H CF₃ H — n-Pr(Z) CH₃G²-2 Cl H CF₃ H — n-Pr CH₃ G²-2 Cl H CF₃ H — n-Pr(Z) CH₃(S) G²-2 Cl HCF₃ H — n-Pr CH₃(S) G²-2 Cl H CF₃ H — n-Pr(Z) H G²-2 Cl H CH═NOCH₃ H —n-Pr H G²-2 Cl H CH═NOEt H — n-Pr H G²-2 Cl H C(CH₃)═NOCH₃ H — n-Pr CH₃G²-2 Cl H C(CH₃)═NOCH₃ H — n-Pr CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — n-Pr HG²-2 Cl H C(CH₃)═NOEt H — n-Pr H G²-2 Cl H C(Et)═NOCH₃ H — n-Pr H G²-2Cl H C≡CH H — n-Pr H G²-2 Cl H C≡CH H — n-Pr(Z) H G²-2 Cl H C≡CCH₃ H —n-Pr H G²-2 Cl H C≡CCH₃ H — n-Pr(Z) H G²-2 Cl H C≡CEt H — n-Pr H G²-2 ClH C≡CPr-n H — n-Pr H G²-2 Cl H C≡CPr-c H — n-Pr H G²-2 Cl H C≡CPr-c H —n-Pr(Z) CH₃ G²-2 Cl H C≡CPr-c H — n-Pr CH₃ G²-2 Cl H C≡CPr-c H — n-Pr(Z)CH₃(S) G²-2 Cl H C≡CPr-c H — n-Pr CH₃(S) G²-2 Cl H C≡CPr-c H — n-Pr(Z) HG²-2 Cl H C≡CBu-n H — n-Pr H G²-2 Cl H C≡CBu-t H — n-Pr H G²-2 Cl HC≡CBu-t H — n-Pr(Z) CH₃ G²-2 Cl H C≡CBu-t H — n-Pr CH₃ G²-2 Cl H C≡CBu-tH — n-Pr(Z) CH₃(S) G²-2 Cl H C≡CBu-t H — n-Pr CH₃(S) G²-2 Cl H C≡CBu-t H— n-Pr(Z) H G²-2 Cl H C≡CPen-c H — n-Pr H G²-2 Cl H C≡CPen-c H — n-Pr(Z)H G²-2 Cl H C≡CCl H — n-Pr H G²-2 Cl H C≡CBr H — n-Pr H G²-2 Cl H C≡Cl H— n-Pr H G²-2 Cl H C≡CC(CH₃)₂OH H — n-Pr H G²-2 Cl H C≡CC(CH₃)₂OH H —n-Pr(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — n-Pr H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H— n-Pr(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — n-Pr H G²-2 Cl H C≡CSi(CH₃)₃ H —n-Pr(Z) H G²-2 Cl H C≡CPh H — n-Pr H G²-2 Cl H C≡CPh H — n-Pr(Z) H G²-2Cl F Cl H — n-Pr H G²-2 Cl F Cl H — n-Pr(Z) CH₃ G²-2 Cl F Cl H — n-Pr(Z)CH₃(S) G²-2 Cl F Cl H — n-Pr(Z) H G²-2 Cl Cl Cl H — n-Pr H G²-2 Cl Cl ClH — n-Pr(Z) CH₃ G²-2 Cl Cl Cl H — n-Pr(Z) CH₃(S) G²-2 Cl Cl Cl H —n-Pr(Z) H G²-2 Br H F H — n-Pr H G²-2 Br H F H — n-Pr(Z) H G²-2 Br H ClH — n-Pr H G²-2 Br H Cl H — n-Pr(Z) CH₃ G²-2 Br H Cl H — n-Pr(Z) CH₃(S)G²-2 Br H Cl H — n-Pr(Z) H G²-2 Br H Br H — n-Pr H G²-2 Br H Br H —n-Pr(Z) CH₃ G²-2 Br H Br H — n-Pr CH₃ G²-2 Br H Br H — n-Pr(Z) CH₃(S)G²-2 Br H Br H — n-Pr CH₃(S) G²-2 Br H Br H — n-Pr(Z) H G²-2 Br H CF₃ H— n-Pr H G²-2 Br H CF₃ H — n-Pr(Z) H G²-6 Cl — Cl H — n-Pr CH₃ G²-6 Cl —Cl H — n-Pr CH₃ G²-9 Cl H Cl — — n-Pr CH₃ G²-9 Cl H Cl — — n-Pr(Z) CH₃G²-9 Cl H Br — — n-Pr CH₃ G²-9 Cl H Br — — n-Pr(Z) CH₃ G²-9 Cl H C≡CPr-c— — n-Pr CH₃ G²-9 Cl H C≡CPr-c — — n-Pr(Z) CH₃ G²-9 Cl H C≡CBu-t — —n-Pr CH₃ G²-9 Cl H C≡CBu-t — — n-Pr(Z) H G²-9 Cl Cl Cl — — n-Pr CH₃ G²-9Cl Cl Cl — — n-Pr CH₃ G²-9 Cl Cl Cl — — n-Pr(Z) CH₃ G²-1 H H Ph H H i-PrCH₃ G²-1 F H Cl H H i-Pr CH₃ G²-1 F H Cl H H i-Pr(E) CH₃(S) G²-1 F H ClH H i-Pr CH₃(S) G²-1 F H Cl H H i-Pr(E) CH₃ G²-1 F H Br H H i-Pr CH₃G²-1 Cl H F H H i-Pr CH₃ G²-1 Cl H F H H i-Pr(E) CH₃(S) G²-1 Cl H F H Hi-Pr CH₃(S) G²-1 Cl H F H H i-Pr(E) H G²-1 Cl H Cl H H i-Pr CH₃ G²-1 ClH Cl H H i-Pr CH₃ G²-1 Cl H Cl H H i-Pr(E) CH₃(S) G²-1 Cl H Cl H H i-PrCH₃(S) G²-1 Cl H Cl H H i-Pr(E) CH₃ G²-1 Cl H Br H H i-Pr CH₃ G²-1 Cl HCH₃ H H i-Pr CH₃ G²-1 Cl H CH₃ H H i-Pr(E) CH₃(S) G²-1 Cl H CH₃ H H i-PrCH₃(S) G²-1 Cl H CH₃ H H i-Pr(E) CH₃ G²-1 CH₃ H OPr-i H H i-Pr H G²-2 HH CF₃ H — i-Pr H G²-2 F H F H — i-Pr H G²-2 F H Cl H — i-Pr H G²-2 F HCl H — i-Pr(Z) CH₃ G²-2 F H Cl H — i-Pr CH₃ G²-2 F H Cl H — i-Pr(Z)CH₃(S) G²-2 F H Cl H — i-Pr CH₃(S) G²-2 F H Cl H — i-Pr(Z) H G²-2 F H ClF — i-Pr H G²-2 F H Cl F — i-Pr(Z) H G²-2 F H Br H — i-Pr H G²-2 F H BrH — i-Pr(Z) CH₃ G²-2 F H Br H — i-Pr(Z) CH₃(S) G²-2 F H Br H — i-Pr(Z) HG²-2 F H I H — i-Pr H G²-2 F H CH₃ H — i-Pr H G²-2 F H CF₃ H — i-Pr HG²-2 F H CF₃ H — i-Pr(Z) H G²-2 F H OCH₂CF₃ H — i-Pr H G²-2 F H NO₂ H —i-Pr H G²-2 F H T-7 H — i-Pr H G²-2 F H T-8 H — i-Pr H G²-2 F H T-9 H —i-Pr H G²-2 F H CN H — i-Pr H G²-2 F H D-3-a H — i-Pr H G²-2 Cl H H H —i-Pr(Z) H G²-2 Cl H F H — i-Pr H G²-2 Cl H F H — i-Pr(Z) CH₃ G²-2 Cl H FH — i-Pr CH₃ G²-2 Cl H F H — i-Pr(Z) CH₃(S) G²-2 Cl H F H — i-Pr CH₃(S)G²-2 Cl H F H — i-Pr(Z) H G²-2 Cl H Cl H — i-Pr H G²-2 Cl H Cl H —i-Pr(E) H G²-2 Cl H Cl H — i-Pr(Z) CH₃ G²-2 Cl H Cl H — i-Pr CH₃ G²-2 ClH Cl H — i-Pr(E) CH₃ G²-2 Cl H Cl H — i-Pr(Z) CH₃(R) G²-2 Cl H Cl H —i-Pr CH₃(R) G²-2 Cl H Cl H — i-Pr(E) CH₃(R) G²-2 Cl H Cl H — i-Pr(Z)CH₃(S) G²-2 Cl H Cl H — i-Pr CH₃(S) G²-2 Cl H Cl H — i-Pr(E) CH₃(S) G²-2Cl H Cl H — i-Pr(Z) CH₂F G²-2 Cl H Cl H — i-Pr H G²-2 Cl H Cl F — i-Pr HG²-2 Cl H Cl F — i-Pr(Z) CH₃ G²-2 Cl H Cl F — i-Pr CH₃ G²-2 Cl H Cl F —i-Pr(Z) CH₃(S) G²-2 Cl H Cl F — i-Pr CH₃(S) G²-2 Cl H Cl F — i-Pr(Z) HG²-2 Cl H Cl Cl — i-Pr H G²-2 Cl H Cl Cl — i-Pr(Z) H G²-2 Cl H Cl OCH₃ —i-Pr H G²-2 Cl H Br H — i-Pr H G²-2 Cl H Br H — i-Pr(Z) CH₃ G²-2 Cl H BrH — i-Pr CH₃ G²-2 Cl H Br H — i-Pr(Z) CH₃(S) G²-2 Cl H Br H — i-PrCH₃(S) G²-2 Cl H Br H — i-Pr(Z) H G²-2 Cl H CH₃ H — i-Pr H G²-2 Cl H CH₃H — i-Pr(Z) CH₃ G²-2 Cl H CH₃ H — i-Pr(Z) CH₃(S) G²-2 Cl H CH₃ H —i-Pr(Z) H G²-2 Cl H CHF₂ H — i-Pr H G²-2 Cl H CHF₂ H — i-Pr(Z) CH₃ G²-2Cl H CHF₂ H — i-Pr(Z) CH₃(S) G²-2 Cl H CHF₂ H — i-Pr(Z) H G²-2 Cl H CF₃H — i-Pr H G²-2 Cl H CF₃ H — i-Pr(E) H G²-2 Cl H CF₃ H — i-Pr(Z) CH₃G²-2 Cl H CF₃ H — i-Pr CH₃ G²-2 Cl H CF₃ H — i-Pr(Z) CH₃(R) G²-2 Cl HCF₃ H — i-Pr CH₃(R) G²-2 Cl H CF₃ H — i-Pr(Z) CH₃(S) G²-2 Cl H CF₃ H —i-Pr CH₃(S) G²-2 Cl H CF₃ H — i-Pr(Z) H G²-2 Cl H CH₂OCH₃ H — i-Pr HG²-2 Cl H OCH₃ H — i-Pr H G²-2 Cl H OCHF₂ H — i-Pr H G²-2 Cl H OCF₃ H —i-Pr H G²-2 Cl H OCF₂Cl H — i-Pr H G²-2 Cl H OCF₂Br H — i-Pr H G²-2 Cl HO(Ph-4-Cl) H — i-Pr(Z) H G²-2 Cl H SCH₃ H — i-Pr H G²-2 Cl H NO₂ H —i-Pr H G²-2 Cl H CH═NOCH₃ H — i-Pr H G²-2 Cl H CH═NOEt H — i-Pr CH₃ G²-2Cl H CH═NOEt H — i-Pr CH₃(S) G²-2 Cl H CH═NOEt H — i-Pr H G²-2 Cl HC(CH₃)═NOCH₃ H — i-Pr CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H — i-Pr CH₃(S) G²-2 ClH C(CH₃)═NOCH₃ H — i-Pr H G²-2 Cl H C(CH₃)═NOEt H — i-Pr CH₃ G²-2 Cl HC(CH₃)═NOEt H — i-Pr CH₃(S) G²-2 Cl H C(CH₃)═NOEt H — i-Pr H G²-2 Cl HC(Et)═NOCH₃ H — i-Pr CH₃ G²-2 Cl H C(Et)═NOCH₃ H — i-Pr CH₃(S) G²-2 Cl HC(Et)═NOCH₃ H — i-Pr H G²-2 Cl H C(Et)═NOEt H — i-Pr H G²-2 Cl H(M-3-b)CH₃ H — i-Pr H G²-2 Cl H CN H — i-Pr H G²-2 Cl H CN H — i-Pr(Z)CH₃ G²-2 Cl H CN H — i-Pr(Z) CH₃(S) G²-2 Cl H CN H — i-Pr(Z) H G²-2 Cl HC(O)NH₂ H — i-Pr H G²-2 Cl H C(S)NH₂ H — i-Pr H G²-2 Cl H M-7-a H — i-PrH G²-2 Cl H M-9-a H — i-Pr H G²-2 Cl H M-17-a H — i-Pr H G²-2 Cl HM-19-a H — i-Pr H G²-2 Cl H CH═CH₂ H — i-Pr H G²-2 Cl H C≡CH H — i-Pr HG²-2 Cl H C≡CH H — i-Pr(Z) CH₃ G²-2 Cl H C≡CH H — i-Pr CH₃ G²-2 Cl HC≡CH H — i-Pr(Z) CH₃(S) G²-2 Cl H C≡CH H — i-Pr CH₃(S) G²-2 Cl H C≡CH H— i-Pr(Z) H G²-2 Cl H C≡CCH₃ H — i-Pr H G²-2 Cl H C≡CCH₃ H — i-Pr(Z) HG²-2 Cl H C≡CEt H — i-Pr H G²-2 Cl H C≡CPr-n H — i-Pr H G²-2 Cl HC≡CPr-i H — i-Pr H G²-2 Cl H C≡CPr-c H — i-Pr H G²-2 Cl H C≡CPr-c H —i-Pr(Z) CH₃ G²-2 Cl H C≡CPr-c H — i-Pr CH₃ G²-2 Cl H C≡CPr-c H — i-Pr(Z)CH₃(S) G²-2 Cl H C≡CPr-c H — i-Pr CH₃(S) G²-2 Cl H C≡CPr-c H — i-Pr(Z) HG²-2 Cl H C≡CBu-n H — i-Pr H G²-2 Cl H C≡CBu-i H — i-Pr H G²-2 Cl HC≡CBu-s H — i-Pr H G²-2 Cl H C≡CBu-t H — i-Pr H G²-2 Cl H C≡CBu-t H —i-Pr(Z) CH₃ G²-2 Cl H C≡CBu-t H — i-Pr CH₃ G²-2 Cl H C≡CBu-t H — i-Pr(Z)CH₃(S) G²-2 Cl H C≡CBu-t H — i-Pr CH₃(S) G²-2 Cl H C≡CBu-t H — i-Pr(Z) HG²-2 Cl H C≡CPen-c H — i-Pr H G²-2 Cl H C≡CPen-c H — i-Pr(Z) H G²-2 Cl HC≡CCl H — i-Pr H G²-2 Cl H C≡CBr H — i-Pr H G²-2 Cl H C≡CI H — i-Pr HG²-2 Cl H C≡CC(CH₃)₂F H — i-Pr H G²-2 Cl H C≡CC(CH₃)₂Cl H — i-Pr H G²-2Cl H C≡CC(CH₃)₂Cl H — i-Pr(Z) H G²-2 Cl H C≡CC(CH₃)₂Br H — i-Pr H G²-2Cl H C≡CCH₂OCH₃ H — i-Pr H G²-2 Cl H C≡CC(CH₃)₂OH H — i-Pr H G²-2 Cl HC≡CC(CH₃)₂OH H — i-Pr(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — i-Pr H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — i-Pr(Z) H G²-2 Cl H C≡CC(CH₃)₂OEt H — i-Pr H G²-2 ClH C≡CC(CH₃)₂OEt H — i-Pr(Z) H G²-2 Cl H C≡C(T-3) H — i-Pr H G²-2 Cl HC≡C(T-4) H — i-Pr H G²-2 Cl H C≡CCH₂SCH₃ H — i-Pr H G²-2 Cl HC≡CCH₂S(O)CH₃ H — i-Pr H G²-2 Cl H C≡CCH₂SO₂CH₃ H — i-Pr H G²-2 Cl HC≡CC(CH₃)₂SEt H — i-Pr H G²-2 Cl H C≡CC(CH₃)₂SEt H — i-Pr(Z) H G²-2 Cl HC≡CSi(CH₃)₃ H — i-Pr H G²-2 Cl H C≡CSi(CH₃)₃ H — i-Pr(Z) H G²-2 Cl HC≡C(T-5) H — i-Pr H G²-2 Cl H C≡C(T-6) H — i-Pr H G²-2 Cl H C≡CPh H —i-Pr H G²-2 Cl H C≡CPh H — i-Pr(Z) H G²-2 Cl H C≡C(Ph-2-F) H — i-Pr HG²-2 Cl H C≡C(Ph-3-F) H — i-Pr H G²-2 Cl H C≡C(Ph-4-F) H — i-Pr H G²-2Cl H C≡C(Ph-2-Cl) H — i-Pr H G²-2 Cl H C≡C(Ph-3-Cl) H — i-Pr H G²-2 Cl HC≡C(Ph-4-Cl) H — i-Pr H G²-2 Cl H C≡C(Ph-2-CH₃) H — i-Pr H G²-2 Cl HC≡C(Ph-3-CH₃) H — i-Pr H G²-2 Cl H C≡C(Ph-4-CH₃) H — i-Pr H G²-2 Cl HC≡C(Ph-4-Bu-t) H — i-Pr H G²-2 Cl H C≡C(Ph-2-CF₃) H — i-Pr H G²-2 Cl HC≡C(Ph-3-CF₃) H — i-Pr H G²-2 Cl H C≡C(Ph-4-CF₃) H — i-Pr H G²-2 Cl HC≡C(Ph-2-OCH₃) H — i-Pr H G²-2 Cl H C≡C(Ph-3-OCH₃) H — i-Pr H G²-2 Cl HC≡C(Ph-4-OCH₃) H — i-Pr H G²-2 Cl H C≡C(Ph-4-OCF₃) H — i-Pr H G²-2 Cl HC≡C(Ph-4-NO₂) H — i-Pr H G²-2 Cl H C≡C(Ph-4-CN) H — i-Pr H G²-2 Cl HC≡C(Ph-2,4-F₂) H — i-Pr H G²-2 Cl H C≡C(Ph-3,4-F₂) H — i-Pr H G²-2 Cl HC≡C(Ph-3,5-F₂) H — i-Pr H G²-2 Cl H C≡C(1-Naph) H — i-Pr H G²-2 Cl HC≡C(D-2-2a) H — i-Pr H G²-2 Cl H C≡C(D-12-3a)CH₃ H — i-Pr H G²-2 Cl HC≡C(D-32-1a) H — i-Pr H G²-2 Cl H C≡C(D-32-2a) H — i-Pr H G²-2 Cl HC≡C(D-32-3a) H — i-Pr H G²-2 Cl H Ph-4-F H — i-Pr H G²-2 Cl H D-3-a H —i-Pr H G²-2 Cl H D-3-a H — i-Pr(Z) H G²-2 Cl H D-7-a H — i-Pr H G²-2 ClH D-11-a H — i-Pr H G²-2 Cl H D-22-a H — i-Pr H G²-2 Cl H D-28-a H —i-Pr H G²-2 Cl H D-29-a H — i-Pr H G²-2 Cl F Cl H — i-Pr H G²-2 Cl F ClH — i-Pr(Z) CH₃ G²-2 Cl F Cl H — i-Pr CH₃ G²-2 Cl F Cl H — i-Pr(Z)CH₃(S) G²-2 Cl F Cl H — i-Pr CH₃(S) G²-2 Cl F Cl H — i-Pr(Z) H G²-2 ClCl Cl H — i-Pr H G²-2 Cl Cl Cl H — i-Pr(Z) CH₃ G²-2 Cl Cl Cl H — i-PrCH₃ G²-2 Cl Cl Cl H — i-Pr(Z) CH₃(S) G²-2 Cl Cl Cl H — i-Pr CH₃(S) G²-2Cl Cl Cl H — i-Pr(Z) H G²-2 Cl Br Cl H — i-Pr H G²-2 Cl Br Cl H —i-Pr(Z) H G²-2 Cl I Cl H — i-Pr H G²-2 Cl CH₃ Cl H — i-Pr H G²-2 Cl CH₃Cl H — i-Pr(Z) H G²-2 Cl CH₂OCH₃ Cl H — i-Pr H G²-2 Cl CH₂SCH₃ Cl H —i-Pr H G²-2 Cl CH₂SO₂CH₃ Cl H — i-Pr H G²-2 Cl OCH₃ Cl H — i-Pr H G²-2Cl SCH₃ Cl H — i-Pr H G²-2 Cl SO₂CH₃ Cl H — i-Pr H G²-2 Cl CN Cl H —i-Pr H G²-2 Cl CN Cl H — i-Pr(Z) H G²-2 Cl C(O)OCH₃ Cl H — i-Pr H G²-2Br H F H — i-Pr H G²-2 Br H F H — i-Pr(Z) CH₃ G²-2 Br H F H — i-Pr(Z)CH₃(S) G²-2 Br H F H — i-Pr(Z) H G²-2 Br H Cl H — i-Pr H G²-2 Br H Cl H— i-Pr(Z) CH₃ G²-2 Br H Cl H — i-Pr CH₃ G²-2 Br H Cl H — i-Pr(Z) CH₃(S)G²-2 Br H Cl H — i-Pr CH₃(S) G²-2 Br H Cl H — i-Pr(Z) H G²-2 Br H Br H —i-Pr H G²-2 Br H Br H — i-Pr(Z) CH₃ G²-2 Br H Br H — i-Pr CH₃ G²-2 Br HBr H — i-Pr(Z) CH₃(S) G²-2 Br H Br H — i-Pr CH₃(S) G²-2 Br H Br H —i-Pr(Z) H G²-2 Br H CH₃ H — i-Pr H G²-2 Br H CF₃ H — i-Pr H G²-2 Br HCF₃ H — i-Pr(Z) H G₂-2 Br H OCH₃ H — i-Pr H G²-2 Br H OCHF₂ H — i-Pr HG²-2 Br H NO₂ H — i-Pr H G²-2 Br H CN H — i-Pr H G²-2 Br H C(O)NH₂ H —i-Pr H G²-2 Br H C(S)NH₂ H — i-Pr H G²-2 Br H SO₂N(CH₃)₂ H — i-Pr H G²-2Br CH₃ Br H — i-Pr H G²-2 I H CF₃ H — i-Pr H G²-2 CH₃ H F H — i-Pr HG²-2 CH₃ H F H — i-Pr(Z) H G²-2 CH₃ H Cl H — i-Pr H G²-2 CH₃ H Cl H —i-Pr(Z) H G²-2 CH₃ H Br H — i-Pr H G²-2 CH₃ H I H — i-Pr H G²-2 CH₃ HCH₃ H — i-Pr CH₃ G²-2 CH₃ H CH₃ H — i-Pr H G²-2 CH₃ H CF₃ H — i-Pr HG²-2 CH₃ H OCH₃ H — i-Pr H G²-2 CH₃ H OCH₂CF₃ H — i-Pr H G²-2 CH₃ H NO₂H — i-Pr H G²-2 CH₃ H CN H — i-Pr H G²-2 CH₃ H C(O)NH₂ H — i-Pr H G²-2CH₃ H C(S)NH₂ H — i-Pr H G²-2 CF₃ H Br H — i-Pr H G²-2 CF₃ H CH₃ H —i-Pr H G²-2 CF₃ H CF₃ H — i-Pr H G²-2 CF₃ H NO₂ H — i-Pr H G²-2 CF₃ H CNH — i-Pr H G²-2 CF₃ H D-3-a H — i-Pr H G²-2 OCH₃ H Cl H — i-Pr H G²-2OCH₃ H Br H — i-Pr H G²-2 OCHF₂ H Cl H — i-Pr H G²-2 OCHF₂ H Br H — i-PrH G²-2 SCH₃ H Br H — i-Pr H G²-2 NO₂ H Cl H — i-Pr H G²-2 NO₂ H Br H —i-Pr H G²-2 NO₂ H CF₃ H — i-Pr H G²-2 CN H Cl H — i-Pr H G²-2 CN H Br H— i-Pr H G²-2 CN H CH₃ H — i-Pr H G²-2 CN H Et H — i-Pr H G²-2 CN H CF₃H — i-Pr H G²-3 F — F F H i-Pr H G²-3 Cl — H Cl H i-Pr H G²-3 Cl — Cl HH i-Pr CH₃ G²-3 Cl — Cl H H i-Pr H G²-3 Cl — Cl F H i-Pr H G²-3 Cl — CF₃H H i-Pr H G²-3 Br — Br H H i-Pr CH₃ G²-3 CH₃ — Cl H H i-Pr H G²-3 CH₃ —Cl CN H i-Pr H G²-3 CH₃ — CF₃ H H i-Pr H G²-4 Cl H Cl — H i-Pr CH₃ G²-4Cl H Cl — H i-Pr H G²-4 Cl H CF₃ — H i-Pr H G²-4 Cl H C≡CPr-c — H i-PrCH₃ G²-4 Cl H C≡CPr-c — H i-Pr H G²-4 Cl H C≡CBu-t — H i-Pr CH₃ G²-4 ClH C≡CBu-t — H i-Pr CH₃ G²-4 CH₃ H Cl — H i-Pr H G²-6 Cl — Cl H — i-PrCH₃ G²-6 Cl — Cl H — i-Pr H G²-6 CH₃ — Cl H — i-Pr H G²-6 CH₃ — Cl CH₃ —i-Pr H G²-6 CH₃ — CH₃ H — i-Pr H G²-6 CH₃ — C≡CPr-c H — i-Pr H G²-6 CH₃— C≡CBu-t H — i-Pr H G²-7 Cl H Br — — i-Pr CH₃ G²-7 Cl H Br — — i-Pr HG²-7 Cl H C≡CPr-c — — i-Pr CH₃ G²-7 Cl H C≡CPr-c — — i-Pr H G²-7 Cl HC≡CBu-t — — i-Pr CH₃ G²-7 Cl H C≡CBu-t — — i-Pr H G²-7 Cl Cl Cl — — i-PrCH₃ G²-9 Cl H Cl — — i-Pr CH₃ G²-9 Cl H Cl — — i-Pr(Z) CH₃ G²-9 Cl H Br— — i-Pr CH₃ G²-9 Cl H Br — — i-Pr(Z) CH₃ G²-9 Cl H C≡CPr-c — — i-Pr CH₃G²-9 Cl H C≡CPr-c — — i-Pr(Z) CH₃ G²-9 Cl H C≡CBu-t — — i-Pr CH₃ G²-9 ClH C≡CBu-t — — i-Pr(Z) H G²-9 Cl Cl Cl — — i-Pr CH₃ G²-9 Cl Cl Cl — —i-Pr CH₃ G²-9 Cl Cl Cl — — i-Pr(Z) H G²-2 Cl H Cl H — c-Pr H G²-2 Cl HCF₃ H — c-Pr H G²-2 F H Cl H — n-Bu H G²-2 F H Cl H — n-Bu(Z) H G²-2 ClH F H — n-Bu H G²-2 Cl H F H — n-Bu(Z) H G²-2 Cl H Cl H — n-Bu H G²-2 ClH Cl H — n-Bu(Z) CH₃ G²-2 Cl H Cl H — n-Bu CH₃ G²-2 Cl H Cl H — n-Bu(Z)CH₃(S) G²-2 Cl H Cl H — n-Bu CH₃(S) G²-2 Cl H Cl H — n-Bu(Z) H G²-2 Cl HCl F — n-Bu H G²-2 Cl H Cl F — n-Bu(Z) CH₃ G²-2 Cl H Cl F — n-Bu(Z)CH₃(S) G²-2 Cl H Cl F — n-Bu(Z) H G²-2 Cl H Br H — n-Bu H G²-2 Cl H Br H— n-Bu(Z) CH₃ G²-2 Cl H Br H — n-Bu(Z) CH₃(S) G²-2 Cl H Br H — n-Bu(Z) HG²-2 Cl H CF₃ H — n-Bu H G²-2 Cl H CF₃ H — n-Bu(Z) CH₃ G²-2 Cl H CF₃ H —n-Bu(Z) CH₃(S) G²-2 Cl H CF₃ H — n-Bu(Z) H G²-2 Cl H C≡CH H — n-Bu HG²-2 Cl H C≡CH H — n-Bu(Z) H G²-2 Cl H C≡CCH₃ H — n-Bu H G²-2 Cl HC≡CCH₃ H — n-Bu(Z) H G²-2 Cl H C≡CEt H — n-Bu H G²-2 Cl H C≡CPr-n H —n-Bu H G²-2 Cl H C≡CPr-c H — n-Bu H G²-2 Cl H C≡CPr-c H — n-Bu(Z) CH₃G²-2 Cl H C≡CPr-c H — n-Bu CH₃ G²-2 Cl H C≡CPr-c H — n-Bu(Z) CH₃(S) G²-2Cl H C≡CPr-c H — n-Bu CH₃(S) G²-2 Cl H C≡CPr-c H — n-Bu(Z) H G²-2 Cl HC≡CBu-n H — n-Bu H G²-2 Cl H C≡CBu-t H — n-Bu H G²-2 Cl H C≡CBu-t H —n-Bu(Z) CH₃ G²-2 Cl H C≡CBu-t H — n-Bu(Z) CH₃(S) G²-2 Cl H C≡CBu-t H —n-Bu(Z) H G²-2 Cl H C≡CPen-c H — n-Bu H G²-2 Cl H C≡CPen-c H — n-Bu(Z) HG²-2 Cl H C≡CCl H — n-Bu H G²-2 Cl H C≡CBr H — n-Bu H G²-2 Cl H C≡CI H —n-Bu H G²-2 Cl H C≡CC(CH₃)₂OH H — n-Bu H G²-2 Cl H C≡CC(CH₃)₂OH H —n-Bu(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — n-Bu H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H— n-Bu(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — n-Bu H G²-2 Cl H C≡CSi(CH₃)₃ H —n-Bu(Z) H G²-2 Cl H C≡CPh H — n-Bu H G²-2 Cl H C≡CPh H — n-Bu(Z) H G²-2Cl F Cl H — n-Bu H G²-2 Cl F Cl H — n-Bu(Z) H G²-2 Cl Cl Cl H — n-Bu HG²-2 Cl Cl Cl H — n-Bu(Z) H G²-2 Br H Cl H — n-Bu H G²-2 Br H Cl H —n-Bu(Z) H G²-2 Br H Br H — n-Bu H G²-2 Br H Br H — n-Bu(Z) CH₃ G²-2 Br HBr H — n-Bu(Z) CH₃(S) G²-2 Br H Br H — n-Bu(Z) H G²-2 F H Cl H — i-Bu HG²-2 F H Cl H — i-Bu(Z) H G²-2 Cl H F H — i-Bu H G²-2 Cl H F H — i-Bu(Z)H G²-2 Cl H Cl H — i-Bu H G²-2 Cl H Cl H — i-Bu(Z) CH₃ G²-2 Cl H Cl H —i-Bu CH₃ G²-2 Cl H Cl H — i-Bu(Z) CH₃(S) G²-2 Cl H Cl H — i-Bu CH₃(S)G²-2 Cl H Cl H — i-Bu(Z) H G²-2 Cl H Cl F — i-Bu H G²-2 Cl H Cl F —i-Bu(Z) CH₃ G²-2 Cl H Cl F — i-Bu(Z) CH₃(S) G²-2 Cl H Cl F — i-Bu(Z) HG²-2 Cl H Br H — i-Bu H G²-2 Cl H Br H — i-Bu(Z) CH₃ G²-2 Cl H Br H —i-Bu(Z) CH₃(S) G²-2 Cl H Br H — i-Bu(Z) H G²-2 Cl H CF₃ H — i-Bu H G²-2Cl H CF₃ H — i-Bu(Z) CH₃ G²-2 Cl H CF₃ H — i-Bu(Z) CH₃(S) G²-2 Cl H CF₃H — i-Bu(Z) H G²-2 Cl H C≡CH H — i-Bu H G²-2 Cl H C≡CH H — i-Bu(Z) HG²-2 Cl H C≡CPr-c H — i-Bu H G²-2 Cl H C≡CPr-c H — i-Bu(Z) H G²-2 Cl HC≡CBu-t H — i-Bu H G²-2 Cl H C≡CBu-t H — i-Bu(Z) H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — i-Bu H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — i-Bu(Z) H G²-2 ClH C≡CSi(CH₃)₃ H — i-Bu H G²-2 Cl H C≡CSi(CH₃)₃ H — i-Bu(Z) H G²-2 Cl HC≡CPh H — i-Bu H G²-2 Cl H C≡CPh H — i-Bu(Z) H G²-2 Cl F Cl H — i-Bu HG²-2 Cl F Cl H — i-Bu(Z) H G²-2 Cl Cl Cl H — i-Bu H G²-2 Cl Cl Cl H —i-Bu(Z) H G²-2 Br H Cl H — i-Bu H G²-2 Br H Cl H — i-Bu(Z) H G²-2 Br HBr H — i-Bu H G²-2 Br H Br H — i-Bu(Z) CH₃ G²-2 Br H Br H — i-Bu(Z)CH₃(S) G²-2 Br H Br H — i-Bu(Z) CH₃ G²-1 H H CF₃ H H CH₂Pr-c CH₃ G²-1 HH OCF₃ H H CH₂Pr-c CH₃ G²-1 H H Ph H H CH₂Pr-c CH₃ G²-1 H F F F HCH₂Pr-c CH₃ G²-1 H Cl Cl H H CH₂Pr-c CH₃ G²-1 F H F H H CH₂Pr-c CH₃ G²-1F H F H F CH₂Pr-c CH₃ G²-1 F H Br H H CH₂Pr-c CH₃ G²-1 Cl H F H HCH₂Pr-c CH₃ G²-1 Cl H F H H CH₂Pr-c(E) CH₃(S) G²-1 Cl H F H H CH₂Pr-cCH₃(S) G²-1 Cl H F H H CH₂Pr-c(E) CH₃ G²-1 Cl H Br H H CH₂Pr-c H G²-2 FH Cl H — CH₂Pr-c H G²-2 F H Cl H — CH₂Pr-c(Z) CH₃ G²-2 F H Cl H —CH₂Pr-c(Z) CH₃(S) G²-2 F H Cl H — CH₂Pr-c(Z) H G²-2 F H Br H — CH₂Pr-c HG²-2 F H Br H — CH₂Pr-c(Z) CH₃ G²-2 F H Br H — CH₂Pr-c(Z) CH₃(S) G²-2 FH Br H — CH₂Pr-c(Z) H G²-2 F H CF₃ H — CH₂Pr-c H G²-2 F H CF₃ H —CH₂Pr-c(Z) H G²-2 Cl H F H — CH₂Pr-c H G²-2 Cl H F H — CH₂Pr-c(Z) CH₃G²-2 Cl H F H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl H F H — CH₂Pr-c(Z) H G²-2 Cl HCl H — CH₂Pr-c H G²-2 Cl H Cl H — CH₂Pr-c(Z) CH₃ G²-2 Cl H Cl H —CH₂Pr-c CH₃ G²-2 Cl H Cl H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl H Cl H — CH₂Pr-cCH₃(S) G²-2 Cl H Cl H — CH₂Pr-c(Z) H G²-2 Cl H Cl F — CH₂Pr-c H G²-2 ClH Cl F — CH₂Pr-c(Z) CH₃ G²-2 Cl H Cl F — CH₂Pr-c CH₃ G²-2 Cl H Cl F —CH₂Pr-c(Z) CH₃(S) G²-2 Cl H Cl F — CH₂Pr-c CH₃(S) G²-2 Cl H Cl F —CH₂Pr-c(Z) H G²-2 Cl H Cl Cl — CH₂Pr-c H G²-2 Cl H Cl Cl — CH₂Pr-c(Z) HG²-2 Cl H Br H — CH₂Pr-c H G²-2 Cl H Br H — CH₂Pr-c(Z) CH₃ G²-2 Cl H BrH — CH₂Pr-c CH₃ G²-2 Cl H Br H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl H Br H —CH₂Pr-c CH₃(S) G²-2 Cl H Br H — CH₂Pr-c(Z) H G²-2 Cl H CF₃ H — CH₂Pr-c HG²-2 Cl H CF₃ H — CH₂Pr-c(E) H G²-2 Cl H CF₃ H — CH₂Pr-c(Z) CH₃ G²-2 ClH CF₃ H — CH₂Pr-c CH₃ G²-2 Cl H CF₃ H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl H CF₃H — CH₂Pr-c CH₃(S) G²-2 Cl H CF₃ H — CH₂Pr-c(Z) H G²-2 Cl H CH═NOCH₃ H —CH₂Pr-c H G²-2 Cl H CH═NOEt H — CH₂Pr-c H G²-2 Cl H C(CH₃)═NOCH₃ H —CH₂Pr-c CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂Pr-c CH₃(S) G²-2 Cl HC(CH₃)═NOCH₃ H — CH₂Pr-c H G²-2 Cl H C(CH₃)═NOEt H — CH₂Pr-c H G²-2 Cl HC(Et)═NOCH₃ H — CH₂Pr-c H G²-2 Cl H C≡CH H — CH₂Pr-c H G²-2 Cl H C≡CH H— CH₂Pr-c(Z) H G²-2 Cl H C≡CCH₃ H — CH₂Pr-c H G²-2 Cl H C≡CCH₃ H —CH₂Pr-c(Z) H G²-2 Cl H C≡CEt H — CH₂Pr-c H G²-2 Cl H C≡CPr-n H — CH₂Pr-cH G²-2 Cl H C≡CPr-c H — CH₂Pr-c H G²-2 Cl H C≡CPr-c H — CH₂Pr-c(Z) CH₃G²-2 Cl H C≡CPr-c H — CH₂Pr-c CH₃ G²-2 Cl H C≡CPr-c H — CH₂Pr-c(Z)CH₃(S) G²-2 Cl H C≡CPr-c H — CH₂Pr-c CH₃(S) G²-2 Cl H C≡CPr-c H —CH₂Pr-c(Z) H G²-2 Cl H C≡CBu-n H — CH₂Pr-c H G²-2 Cl H C≡CBu-t H —CH₂Pr-c H G²-2 Cl H C≡CBu-t H — CH₂Pr-c(Z) CH₃ G²-2 Cl H C≡CBu-t H —CH₂Pr-c CH₃ G²-2 Cl H C≡CBu-t H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl H C≡CBu-t H— CH₂Pr-c CH₃(S) G²-2 Cl H C≡CBu-t H — CH₂Pr-c(Z) H G²-2 Cl H C≡CPen-c H— CH₂Pr-c H G²-2 Cl H C≡CPen-c H — CH₂Pr-c(Z) H G²-2 Cl H C≡CCl H —CH₂Pr-c H G²-2 Cl H C≡CBr H — CH₂Pr-c H G²-2 Cl H C≡CI H — CH₂Pr-c HG²-2 Cl H C≡CC(CH₃)₂OH H — CH₂Pr-c H G²-2 Cl H C≡CC(CH₃)₂OH H —CH₂Pr-c(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂Pr-c H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — CH₂Pr-c(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂Pr-c H G²-2Cl H C≡CSi(CH₃)₃ H — CH₂Pr-c(Z) H G²-2 Cl H C≡CPh H — CH₂Pr-c H G²-2 ClH C≡CPh H — CH₂Pr-c(Z) H G²-2 Cl H CN H — CH₂Pr-c H G²-2 Cl F Cl H —CH₂Pr-c H G²-2 Cl F Cl H — CH₂Pr-c(Z) CH₃ G²-2 Cl F Cl H — CH₂Pr-c(Z)CH₃(S) G²-2 Cl F Cl H — CH₂Pr-c(Z) H G²-2 Cl Cl Cl H — CH₂Pr-c H G²-2 ClCl Cl H — CH₂Pr-c(Z) CH₃ G²-2 Cl Cl Cl H — CH₂Pr-c(Z) CH₃(S) G²-2 Cl ClCl H — CH₂Pr-c(Z) H G²-2 Br H F H — CH₂Pr-c H G²-2 Br H F H — CH₂Pr-c(Z)H G²-2 Br H Cl H — CH₂Pr-c H G²-2 Br H Cl H — CH₂Pr-c(Z) CH₃ G²-2 Br HCl H — CH₂Pr-c(Z) CH₃(S) G²-2 Br H Cl H — CH₂Pr-c(Z) H G²-2 Br H Br H —CH₂Pr-c H G²-2 Br H Br H — CH₂Pr-c(Z) CH₃ G²-2 Br H Br H — CH₂Pr-c CH₃G²-2 Br H Br H — CH₂Pr-c(Z) CH₃(S) G²-2 Br H Br H — CH₂Pr-c CH₃(S) G²-2Br H Br H — CH₂Pr-c(Z) H G²-2 Br H CF₃ H — CH₂Pr-c H G²-2 Br H CF₃ H —CH₂Pr-c(Z) H G²-6 Cl — Cl H — CH₂Pr-c CH₃ G²-6 Cl — Cl H — CH₂Pr-c CH₃G²-9 Cl H Cl — — CH₂Pr-c CH₃ G²-9 Cl H Cl — — CH₂Pr-c(Z) CH₃ G²-9 Cl HBr — — CH₂Pr-c CH₃ G²-9 Cl H Br — — CH₂Pr-c(Z) CH₃ G²-9 Cl H C≡CPr-c — —CH₂Pr-c CH₃ G²-9 Cl H C≡CPr-c — — CH₂Pr-c(Z) CH₃ G²-9 Cl H C≡CBu-t — —CH₂Pr-c CH₃ G²-9 Cl H C≡CBu-t — — CH₂Pr-c(Z) CH₃ G²-9 Cl Cl Cl — —CH₂Pr-c CH₃ G²-9 Cl Cl Cl — — CH₂Pr-c(Z) CH₃ G²-1 Cl H F H H s-Bu CH₃G²-1 Cl H F H H s-Bu(E) CH₃(S) G²-1 Cl H F H H s-Bu CH₃(S) G²-1 Cl H F HH s-Bu(E) H G²-2 F H Cl H — s-Bu H G²-2 F H Cl H — s-Bu(Z) CH₃ G²-2 F HCl H — s-Bu(Z) CH₃(S) G²-2 F H Cl H — s-Bu(Z) H G²-2 F H Br H — s-Bu HG²-2 F H Br H — s-Bu(Z) CH₃ G²-2 F H Br H — s-Bu(Z) CH₃(S) G²-2 F H Br H— s-Bu(Z) H G²-2 F H CF₃ H — s-Bu H G²-2 F H CF₃ H — s-Bu(Z) H G²-2 Cl HF H — s-Bu H G²-2 Cl H F H — s-Bu(Z) CH₃ G²-2 Cl H F H — s-Bu(Z) CH₃(S)G²-2 Cl H F H — s-Bu(Z) H G²-2 Cl H Cl H — s-Bu H G²-2 Cl H Cl H —s-Bu(E) H G²-2 Cl H Cl H — s-Bu(Z) CH₃ G²-2 Cl H Cl H — s-Bu CH₃ G²-2 ClH Cl H — s-Bu(Z) CH₃(S) G²-2 Cl H Cl H — s-Bu CH₃(S) G²-2 Cl H Cl H —s-Bu(Z) H G²-2 Cl H Cl F — s-Bu H G²-2 Cl H Cl F — s-Bu(Z) CH₃ G²-2 Cl HCl F — s-Bu CH₃ G²-2 Cl H Cl F — s-Bu(Z) CH₃(S) G²-2 Cl H Cl F — s-BuCH₃(S) G²-2 Cl H Cl F — s-Bu(Z) H G²-2 Cl H Cl Cl — s-Bu H G²-2 Cl H ClCl — s-Bu(Z) H G²-2 Cl H Br H — s-Bu H G²-2 Cl H Br H — s-Bu(Z) CH₃ G²-2Cl H Br H — s-Bu CH₃ G²-2 Cl H Br H — s-Bu(Z) CH₃(S) G²-2 Cl H Br H —s-Bu CH₃(S) G²-2 Cl H Br H — s-Bu(Z) H G²-2 Cl H CF₃ H — s-Bu H G²-2 ClH CF₃ H — s-Bu(Z) CH₃ G²-2 Cl H CF₃ H — s-Bu CH₃ G²-2 Cl H CF₃ H —s-Bu(Z) CH₃(S) G²-2 Cl H CF₃ H — s-Bu CH₃(S) G²-2 Cl H CF₃ H — s-Bu(Z) HG²-2 Cl H CH═NOCH₃ H — s-Bu H G²-2 Cl H CH═NOEt H — s-Bu H G²-2 Cl HC(CH₃)═NOCH₃ H — s-Bu CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H — s-Bu CH₃(S) G²-2 ClH C(CH₃)═NOCH₃ H — s-Bu H G²-2 Cl H C(CH₃)═NOEt H — s-Bu H G²-2 Cl HC(Et)═NOCH₃ H — s-Bu H G²-2 Cl H C≡CH H — s-Bu H G²-2 Cl H C≡CH H —s-Bu(Z) H G²-2 Cl H C≡CCH₃ H — s-Bu H G²-2 Cl H C≡CCH₃ H — s-Bu(Z) HG²-2 Cl H C≡CEt H — s-Bu H G²-2 Cl H C≡CPr-n H — s-Bu H G²-2 Cl HC≡CPr-c H — s-Bu H G²-2 Cl H C≡CPr-c H — s-Bu(Z) CH₃ G²-2 Cl H C≡CPr-c H— s-Bu CH₃ G²-2 Cl H C≡CPr-c H — s-Bu(Z) CH₃(S) G²-2 Cl H C≡CPr-c H —s-Bu CH₃(S) G²-2 Cl H C≡CPr-c H — s-Bu(Z) H G²-2 Cl H C≡CBu-n H — s-Bu HG²-2 Cl H C≡CBu-t H — s-Bu H G²-2 Cl H C≡CBu-t H — s-Bu(Z) CH₃ G²-2 Cl HC≡CBu-t H — s-Bu CH₃ G²-2 Cl H C≡CBu-t H — s-Bu(Z) CH₃(S) G²-2 Cl HC≡CBu-t H — s-Bu CH₃(S) G²-2 Cl H C≡CBu-t H — s-Bu(Z) H G²-2 Cl HC≡CPen-c H — s-Bu H G²-2 Cl H C≡CPen-c H — s-Bu(Z) H G²-2 Cl H C≡CCl H —s-Bu H G²-2 Cl H C≡CBr H — s-Bu H G²-2 Cl H C≡CI H — s-Bu H G²-2 Cl HC≡CC(CH₃)₂OH H — s-Bu H G²-2 Cl H C≡CC(CH₃)₂OH H — s-Bu(Z) H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — s-Bu H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — s-Bu(Z) H G²-2 ClH C≡CSi(CH₃)₃ H — s-Bu H G²-2 Cl H C≡CSi(CH₃)₃ H — s-Bu(Z) H G²-2 Cl HC≡CPh H — s-Bu H G²-2 Cl H C≡CPh H — s-Bu(Z) H G²-2 Cl F Cl H — s-Bu HG²-2 Cl F Cl H — s-Bu(Z) CH₃ G²-2 Cl F Cl H — s-Bu(Z) CH₃(S) G²-2 Cl FCl H — s-Bu(Z) H G²-2 Cl Cl Cl H — s-Bu H G²-2 Cl Cl Cl H — s-Bu(Z) CH₃G²-2 Cl Cl Cl H — s-Bu(Z) CH₃(S) G²-2 Cl Cl Cl H — s-Bu(Z) H G²-2 Br HCl H — s-Bu H G²-2 Br H Cl H — s-Bu(Z) CH₃ G²-2 Br H Cl H — s-Bu(Z)CH₃(S) G²-2 Br H Cl H — s-Bu(Z) H G²-2 Br H Br H — s-Bu H G²-2 Br H Br H— s-Bu(Z) CH₃ G²-2 Br H Br H — s-Bu CH₃ G²-2 Br H Br H — s-Bu(Z) CH₃(S)G²-2 Br H Br H — s-Bu CH₃(S) G²-2 Br H Br H — s-Bu(Z) H G²-2 Br H CF₃ H— s-Bu H G²-2 Br H CF₃ H — s-Bu(Z) H G²-6 Cl — Cl H — s-Bu CH₃ G²-6 Cl —Cl H — s-Bu CH₃ G²-9 Cl H Cl — — s-Bu CH₃ G²-9 Cl H Cl — — s-Bu(Z) CH₃G²-9 Cl H Br — — s-Bu CH₃ G²-9 Cl H Br — — s-Bu(Z) CH₃ G²-9 Cl H C≡CPr-c— — s-Bu CH₃ G²-9 Cl H C≡CPr-c — — s-Bu(Z) CH₃ G²-9 Cl H C≡CBu-t — —s-Bu CH₃ G²-9 Cl H C≡CBu-t — — s-Bu(Z) CH₃ G²-9 Cl Cl Cl — — s-Bu CH₃G²-9 Cl Cl Cl — — s-Bu(Z) H G²-2 Cl H Cl H — c-Bu H G²-2 Cl H Cl H —c-Bu(Z) CH₃ G²-2 Cl H Cl H — c-Bu(Z) CH₃(S) G²-2 Cl H Cl H — c-Bu(Z) HG²-2 Cl H Cl F — c-Bu H G²-2 Cl H Cl F — c-Bu(Z) H G²-2 Cl H Br H — c-BuH G²-2 Cl H Br H — c-Bu(Z) CH₃ G²-2 Cl H Br H — c-Bu(Z) CH₃(S) G²-2 Cl HBr H — c-Bu(Z) H G²-2 Cl H CF₃ H — c-Bu H G²-2 Cl H CF₃ H — c-Bu(Z) CH₃G²-2 Cl H CF₃ H — c-Bu(Z) CH₃(S) G²-2 Cl H CF₃ H — c-Bu(Z) H G²-2 Cl HC≡CPr-c H — c-Bu H G²-2 Cl H C≡CPr-c H — c-Bu(Z) H G²-2 Cl H C≡CBu-t H —c-Bu H G²-2 Cl H C≡CBu-t H — c-Bu(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — c-BuH G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — c-Bu(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — c-BuH G²-2 Cl H C≡CSi(CH₃)₃ H — c-Bu(Z) H G²-2 Cl H C≡CPh H — c-Bu H G²-2 ClH C≡CPh H — c-Bu(Z) H G²-2 Cl F Cl H — c-Bu H G²-2 Cl F Cl H — c-Bu(Z) HG²-2 Br H Cl H — c-Bu H G²-2 Br H Cl H — c-Bu(Z) H G²-2 Br H Br H — c-BuH G²-2 Br H Br H — c-Bu(Z) CH₃ G²-1 Cl H F H H t-Bu CH₃ G²-1 Cl H F H Ht-Bu(E) CH₃(S) G²-1 Cl H F H H t-Bu CH₃(S) G²-1 Cl H F H H t-Bu(E) HG²-2 F H Cl H — t-Bu H G²-2 F H Cl H — t-Bu(Z) CH₃ G²-2 F H Cl H —t-Bu(Z) CH₃(S) G²-2 F H Cl H — t-Bu(Z) H G²-2 F H Br H — t-Bu H G²-2 F HBr H — t-Bu(Z) CH₃ G²-2 F H Br H — t-Bu(Z) CH₃(S) G²-2 F H Br H —t-Bu(Z) H G²-2 F H CF₃ H — t-Bu H G²-2 F H CF₃ H — t-Bu(Z) H G²-2 Cl H FH — t-Bu H G²-2 Cl H F H — t-Bu(Z) CH₃ G²-2 Cl H F H — t-Bu(Z) CH₃(S)G²-2 Cl H F H — t-Bu(Z) H G²-2 Cl H Cl H — t-Bu H G²-2 Cl H Cl H —t-Bu(E) H G²-2 Cl H Cl H — t-Bu(Z) CH₃ G²-2 Cl H Cl H — t-Bu CH₃ G²-2 ClH Cl H — t-Bu(Z) CH₃(S) G²-2 Cl H Cl H — t-Bu CH₃(S) G²-2 Cl H Cl H —t-Bu(Z) H G²-2 Cl H Cl F — t-Bu H G²-2 Cl H Cl F — t-Bu(Z) CH₃ G²-2 Cl HCl F — t-Bu CH₃ G²-2 Cl H Cl F — t-Bu(Z) CH₃(S) G²-2 Cl H Cl F — t-BuCH₃(S) G²-2 Cl H Cl F — t-Bu(Z) H G²-2 Cl H Cl Cl — t-Bu H G²-2 Cl H ClCl — t-Bu(Z) H G²-2 Cl H Br H — t-Bu H G²-2 Cl H Br H — t-Bu(Z) CH₃ G²-2Cl H Br H — t-Bu CH₃ G²-2 Cl H Br H — t-Bu(Z) CH₃(S) G²-2 Cl H Br H —t-Bu CH₃(S) G²-2 Cl H Br H — t-Bu(Z) H G²-2 Cl H CF₃ H — t-Bu H G²-2 ClH CF₃ H — t-Bu(Z) CH₃ G²-2 Cl H CF₃ H — t-Bu CH₃ G²-2 Cl H CF₃ H —t-Bu(Z) CH₃(S) G²-2 Cl H CF₃ H — t-Bu CH₃(S) G²-2 Cl H CF₃ H — t-Bu(Z) HG²-2 Cl H CH═NOCH₃ H — t-Bu H G²-2 Cl H CH═NOEt H — t-Bu H G²-2 Cl HC(CH₃)═NOCH₃ H — t-Bu CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H — t-Bu CH₃(S) G²-2 ClH C(CH₃)═NOCH₃ H — t-Bu H G²-2 Cl H C(CH₃)═NOEt H — t-Bu H G²-2 Cl HC(Et)═NOCH₃ H — t-Bu H G²-2 Cl H C≡CH H — t-Bu H G²-2 Cl H C≡CH H —t-Bu(Z) H G²-2 Cl H C≡CCH₃ H — t-Bu H G²-2 Cl H C≡CCH₃ H — t-Bu(Z) HG²-2 Cl H C≡CEt H — t-Bu H G²-2 Cl H C≡CPr-n H — t-Bu H G²-2 Cl HC≡CPr-c H — t-Bu H G²-2 Cl H C≡CPr-c H — t-Bu(Z) CH₃ G²-2 Cl H C≡CPr-c H— t-Bu CH₃ G²-2 Cl H C≡CPr-c H — t-Bu(Z) CH₃(S) G²-2 Cl H C≡CPr-c H —t-Bu CH₃(S) G²-2 Cl H C≡CPr-c H — t-Bu(Z) H G²-2 Cl H C≡CBu-n H — t-Bu HG²-2 Cl H C≡CBu-t H — t-Bu H G²-2 Cl H C≡CBu-t H — t-Bu(Z) CH₃ G²-2 Cl HC≡CBu-t H — t-Bu CH₃ G²-2 Cl H C≡CBu-t H — t-Bu(Z) CH₃(S) G²-2 Cl HC≡CBu-t H — t-Bu CH₃(S) G²-2 Cl H C≡CBu-t H — t-Bu(Z) H G²-2 Cl HC≡CPen-c H — t-Bu H G²-2 Cl H C≡CPen-c H — t-Bu(Z) H G²-2 Cl H C≡CCl H —t-Bu H G²-2 Cl H C≡CBr H — t-Bu H G²-2 Cl H C≡CI H — t-Bu H G²-2 Cl HC≡CC(CH₃)₂OH H — t-Bu H G²-2 Cl H C≡CC(CH₃)₂OH H — t-Bu(Z) H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — t-Bu H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — t-Bu(Z) H G²-2 ClH C≡CSi(CH₃)₃ H — t-Bu H G²-2 Cl H C≡CSi(CH₃)₃ H — t-Bu(Z) H G²-2 Cl HC≡CPh H — t-Bu H G²-2 Cl H C≡CPh H — t-Bu(Z) H G²-2 Cl F Cl H — t-Bu HG²-2 Cl F Cl H — t-Bu(Z) CH₃ G²-2 Cl F Cl H — t-Bu(Z) CH₃(S) G²-2 Cl FCl H — t-Bu(Z) H G²-2 Cl Cl Cl H — t-Bu H G²-2 Cl Cl Cl H — t-Bu(Z) CH₃G²-2 Cl Cl Cl H — t-Bu(Z) CH₃(S) G²-2 Cl Cl Cl H — t-Bu(Z) H G²-2 Br H FH — t-Bu H G²-2 Br H F H — t-Bu(Z) H G²-2 Br H Cl H — t-Bu H G²-2 Br HCl H — t-Bu(Z) CH₃ G²-2 Br H Cl H — t-Bu(Z) CH₃(S) G²-2 Br H Cl H —t-Bu(Z) H G²-2 Br H Br H — t-Bu H G²-2 Br H Br H — t-Bu(Z) CH₃ G²-2 Br HBr H — t-Bu CH₃ G²-2 Br H Br H — t-Bu(Z) CH₃(S) G²-2 Br H Br H — t-BuCH₃(S) G²-2 Br H Br H — t-Bu(Z) H G²-2 Br H CF₃ H — t-Bu H G²-2 Br H CF₃H — t-Bu(Z) H G²-6 Cl — Cl H — t-Bu CH₃ G²-6 Cl — Cl H — t-Bu CH₃ G²-9Cl H Cl — — t-Bu CH₃ G²-9 Cl H Cl — — t-Bu(Z) CH₃ G²-9 Cl H Br — — t-BuCH₃ G²-9 Cl H Br — — t-Bu(Z) CH₃ G²-9 Cl H C≡CPr-c — — t-Bu CH₃ G²-9 ClH C≡CPr-c — — t-Bu(Z) CH₃ G²-9 Cl H C≡CBu-t — — t-Bu CH₃ G²-9 Cl HC≡CBu-t — — t-Bu(Z) CH₃ G²-9 Cl Cl Cl — — t-Bu CH₃ G²-9 Cl Cl Cl — —t-Bu(Z) H G²-2 Cl H Cl H — Pen H G²-2 Cl H Cl H — Pen(Z) CH₃ G²-2 Cl HCl H — Pen(Z) CH₃(S) G²-2 Cl H Cl H — Pen(Z) H G²-2 Cl H Cl F — Pen HG²-2 Cl H Cl F — Pen(Z) H G²-2 Cl H Br H — Pen H G²-2 Cl H Br H — Pen(Z)CH₃ G²-2 Cl H Br H — Pen(Z) CH₃(S) G²-2 Cl H Br H — Pen(Z) H G²-2 Cl HCF₃ H — Pen H G²-2 Cl H CF₃ H — Pen(Z) CH₃ G²-2 Cl H CF₃ H — Pen(Z)CH₃(S) G²-2 Cl H CF₃ H — Pen(Z) H G²-2 Cl H C≡CPr-c H — Pen H G²-2 Cl HC≡CPr-c H — Pen(Z) H G²-2 Cl H C≡CBu-t H — Pen H G²-2 Cl H C≡CBu-t H —Pen(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — Pen H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —Pen(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — Pen H G²-2 Cl H C≡CSi(CH₃)₃ H —Pen(Z) H G²-2 Cl H C≡CPh H — Pen H G²-2 Cl H C≡CPh H — Pen(Z) H G²-2 ClF Cl H — Pen H G²-2 Cl F Cl H — Pen(Z) H G²-2 Br H Cl H — Pen H G²-2 BrH Cl H — Pen(Z) H G²-2 Br H Br H — Pen H G²-2 Br H Br H — Pen(Z) H G²-2Cl H Cl H — CH₂Bu-c H G²-2 Cl H Cl H — CH₂Bu-c(Z) H G²-2 Cl H CF₃ H —CH₂Bu-c H G²-2 Cl H CF₃ H — CH₂Bu-c(Z) H G²-2 Cl H Cl H — CH(CH₃)Pr-i HG²-2 F H Cl H — CH(Et)₂ H G²-2 F H Cl H — CH(Et)₂(Z) H G²-2 Cl H F H —CH(Et)₂ H G²-2 Cl H F H — CH(Et)₂(Z) H G²-2 Cl H Cl H — CH(Et)₂ H G²-2Cl H Cl H — CH(Et)₂(Z) CH₃ G²-2 Cl H Cl H — CH(Et)₂ CH₃ G²-2 Cl H Cl H —CH(Et)₂(Z) CH₃(S) G²-2 Cl H Cl H — CH(Et)₂ CH₃(S) G²-2 Cl H Cl H —CH(Et)₂(Z) H G²-2 Cl H Cl F — CH(Et)₂ H G²-2 Cl H Cl F — CH(Et)₂(Z) CH₃G²-2 Cl H Cl F — CH(Et)₂(Z) CH₃(S) G²-2 Cl H Cl F — CH(Et)₂(Z) H G²-2 ClH Br H — CH(Et)₂ H G²-2 Cl H Br H — CH(Et)₂(Z) CH₃ G²-2 Cl H Br H —CH(Et)₂(Z) CH₃(S) G²-2 Cl H Br H — CH(Et)₂(Z) H G²-2 Cl H CF₃ H —CH(Et)₂ H G²-2 Cl H CF₃ H — CH(Et)₂(Z) CH₃ G²-2 Cl H CF₃ H — CH(Et)₂(Z)CH₃(S) G²-2 Cl H CF₃ H — CH(Et)₂(Z) H G²-2 Cl H C≡CH H — CH(Et)₂ H G²-2Cl H C≡CH H — CH(Et)₂(Z) H G²-2 Cl H C≡CPr-c H — CH(Et)₂ H G²-2 Cl HC≡CPr-c H — CH(Et)₂(Z) H G²-2 Cl H C≡CBu-t H — CH(Et)₂ H G²-2 Cl HC≡CBu-t H — CH(Et)₂(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH(Et)₂ H G²-2 ClH C≡CC(CH₃)₂OCH₃ H — CH(Et)₂(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH(Et)₂ HG²-2 Cl H C≡CSi(CH₃)₃ H — CH(Et)₂(Z) H G²-2 Cl H C≡CPh H — CH(Et)₂ HG²-2 Cl H C≡CPh H — CH(Et)₂(Z) H G²-2 Cl F Cl H — CH(Et)₂ H G²-2 Cl F ClH — CH(Et)₂(Z) H G²-2 Cl Cl Cl H — CH(Et)₂ H G²-2 Cl Cl Cl H —CH(Et)₂(Z) H G²-2 Br H Cl H — CH(Et)₂ H G²-2 Br H Cl H — CH(Et)₂(Z) HG²-2 Br H Br H — CH(Et)₂ H G²-2 Br H Br H — CH(Et)₂(Z) CH₃ G²-2 Br H BrH — CH(Et)₂(Z) CH₃(S) G²-2 Br H Br H — CH(Et)₂(Z) H G²-2 Cl H Cl H —CH(CH₃)Pr-c H G²-2 Cl H Cl H — CH(CH₃)Pr-c(Z) H G²-2 Cl H CF₃ H —CH(CH₃)Pr-c H G²-2 Cl H CF₃ H — CH(CH₃)Pr-c(Z) H G²-2 F H Cl H — c-Pen HG²-2 F H Cl H — c-Pen(Z) H G²-2 Cl H F H — c-Pen H G²-2 Cl H F H —c-Pen(Z) H G²-2 Cl H Cl H — c-Pen H G²-2 Cl H Cl H — c-Pen(Z) CH₃ G²-2Cl H Cl H — c-Pen CH₃ G²-2 Cl H Cl H — c-Pen(Z) CH₃(S) G²-2 Cl H Cl H —c-Pen CH₃(S) G²-2 Cl H Cl H — c-Pen(Z) H G²-2 Cl H Cl F — c-Pen H G²-2Cl H Cl F — c-Pen(Z) CH₃ G²-2 Cl H Cl F — c-Pen(Z) CH₃(S) G²-2 Cl H Cl F— c-Pen(Z) H G²-2 Cl H Br H — c-Pen H G²-2 Cl H Br H — c-Pen(Z) CH₃ G²-2Cl H Br H — c-Pen(Z) CH₃(S) G²-2 Cl H Br H — c-Pen(Z) H G²-2 Cl H CF₃ H— c-Pen H G²-2 Cl H CF₃ H — c-Pen(Z) CH₃ G²-2 Cl H CF₃ H — c-Pen(Z)CH₃(S) G²-2 Cl H CF₃ H — c-Pen(Z) H G²-2 Cl H C≡CH H — c-Pen H G²-2 Cl HC≡CH H — c-Pen(Z) H G²-2 Cl H C≡CPr-c H — c-Pen H G²-2 Cl H C≡CPr-c H —c-Pen(Z) H G²-2 Cl H C≡CBu-t H — c-Pen H G²-2 Cl H C≡CBu-t H — c-Pen(Z)H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — c-Pen H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —c-Pen(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — c-Pen H G²-2 Cl H C≡CSi(CH₃)₃ H —c-Pen(Z) H G²-2 Cl H C≡CPh H — c-Pen H G²-2 Cl H C≡CPh H — c-Pen(Z) HG²-2 Cl F Cl H — c-Pen H G²-2 Cl F Cl H — c-Pen(Z) H G²-2 Cl Cl Cl H —c-Pen H G²-2 Cl Cl Cl H — c-Pen(Z) H G²-2 Br H Cl H — c-Pen H G²-2 Br HCl H — c-Pen(Z) H G²-2 Br H Br H — c-Pen H G²-2 Br H Br H — c-Pen(Z) CH₃G²-2 Br H Br H — c-Pen(Z) CH₃(S) G²-2 Br H Br H — c-Pen(Z) H G²-3 Cl — HCl H c-Pen H G²-2 Cl H Cl H — Hex H G²-2 Cl H Cl H — Hex(Z) H G²-2 Cl HCF₃ H — Hex H G²-2 Cl H CF₃ H — Hex(Z) H G²-2 Cl H Cl H — CH₂Pen-c HG²-2 Cl H Cl H — CH₂Pen-c(Z) H G²-2 Cl H CF₃ H — CH₂Pen-c H G²-2 Cl HCF₃ H — CH₂Pen-c(Z) H G²-2 Cl H Cl H — c-Hex H G²-2 Cl H Cl H — c-Hex(Z)H G²-2 Cl H CF₃ H — c-Hex H G²-2 Cl H CF₃ H — c-Hex(Z) H G²-2 Cl H Cl H— CH₂Hex-c H G²-2 Cl H Cl H — CH₂Hex-c(Z) CH₃ G²-2 Cl H Cl H —CH₂Hex-c(Z) CH₃(S) G²-2 Cl H Cl H — CH₂Hex-c(Z) H G²-2 Cl H Cl F —CH₂Hex-c H G²-2 Cl H Cl F — CH₂Hex-c(Z) H G²-2 Cl H Br H — CH₂Hex-c HG²-2 Cl H Br H — CH₂Hex-c(Z) CH₃ G²-2 Cl H Br H — CH₂Hex-c(Z) CH₃(S)G²-2 Cl H Br H — CH₂Hex-c(Z) H G²-2 Cl H CF₃ H — CH₂Hex-c H G²-2 Cl HCF₃ H — CH₂Hex-c(Z) CH₃ G²-2 Cl H CF₃ H — CH₂Hex-c(Z) CH₃(S) G²-2 Cl HCF₃ H — CH₂Hex-c(Z) H G²-2 Cl H C≡CPr-c H — CH₂Hex-c H G²-2 Cl H C≡CPr-cH — CH₂Hex-c(Z) H G²-2 Cl H C≡CBu-t H — CH₂Hex-c H G²-2 Cl H C≡CBu-t H —CH₂Hex-c(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂Hex-c H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — CH₂Hex-c(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂Hex-c HG²-2 Cl H C≡CSi(CH₃)₃ H — CH₂Hex-c(Z) H G²-2 Cl H C≡CPh H — CH₂Hex-c HG²-2 Cl H C≡CPh H — CH₂Hex-c(Z) H G²-2 Cl F Cl H — CH₂Hex-c H G²-2 Cl FCl H — CH₂Hex-c(Z) H G²-2 Br H Cl H — CH₂Hex-c H G²-2 Br H Cl H —CH₂Hex-c(Z) H G²-2 Br H Br H — CH₂Hex-c H G²-2 Br H Br H — CH₂Hex-c(Z) HG²-2 Cl H Cl H — CH₂CH₂Cl H G²-2 Cl H Cl H — CH₂CH₂Cl(Z) H G²-2 Cl H CF₃H — CH₂CH₂Cl H G²-2 Cl H CF₃ H — CH₂CH₂Cl(Z) CH₃ G²-1 Cl H F H H CH₂CHF₂CH₃ G²-1 Cl H F H H CH₂CHF₂(E) CH₃(S) G²-1 Cl H F H H CH₂CHF₂ CH₃(S)G²-1 Cl H F H H CH₂CHF₂(E) H G²-2 F H Cl H — CH₂CHF₂ H G²-2 F H Cl H —CH₂CHF₂(Z) CH₃ G²-2 F H Cl H — CH₂CHF₂(Z) CH₃(S) G²-2 F H Cl H —CH₂CHF₂(Z) H G²-2 F H Br H — CH₂CHF₂ H G²-2 F H Br H — CH₂CHF₂(Z) CH₃G²-2 F H Br H — CH₂CHF₂(Z) CH₃(S) G²-2 F H Br H — CH₂CHF₂(Z) H G²-2 F HCF₃ H — CH₂CHF₂ H G²-2 F H CF₃ H — CH₂CHF₂(Z) H G²-2 Cl H F H — CH₂CHF₂H G²-2 Cl H F H — CH₂CHF₂(Z) CH₃ G²-2 Cl H F H — CH₂CHF₂(Z) CH₃(S) G²-2Cl H F H — CH₂CHF₂(Z) H G²-2 Cl H Cl H — CH₂CHF₂ H G²-2 Cl H Cl H —CH₂CHF₂(Z) CH₃ G²-2 Cl H Cl H — CH₂CHF₂ CH₃ G²-2 Cl H Cl H — CH₂CHF₂(Z)CH₃(S) G²-2 Cl H Cl H — CH₂CHF₂ CH₃(S) G²-2 Cl H Cl H — CH₂CHF₂(Z) HG²-2 Cl H Cl F — CH₂CHF₂ H G²-2 Cl H Cl F — CH₂CHF₂(Z) CH₃ G²-2 Cl H ClF — CH₂CHF₂ CH₃ G²-2 Cl H Cl F — CH₂CHF₂(Z) CH₃(S) G²-2 Cl H Cl F —CH₂CHF₂ CH₃(S) G²-2 Cl H Cl F — CH₂CHF₂(Z) H G²-2 Cl H Cl Cl — CH₂CHF₂ HG²-2 Cl H Cl Cl — CH₂CHF₂(Z) H G²-2 Cl H Br H — CH₂CHF₂ H G²-2 Cl H Br H— CH₂CHF₂(Z) CH₃ G²-2 Cl H Br H — CH₂CHF₂ CH₃ G²-2 Cl H Br H —CH₂CHF₂(Z) CH₃(S) G²-2 Cl H Br H — CH₂CHF₂ CH₃(S) G²-2 Cl H Br H —CH₂CHF₂(Z) H G²-2 Cl H CF₃ H — CH₂CHF₂ H G²-2 Cl H CF₃ H — CH₂CHF₂(E) HG²-2 Cl H CF₃ H — CH₂CHF₂(Z) CH₃ G²-2 Cl H CF₃ H — CH₂CHF₂ CH₃ G²-2 Cl HCF₃ H — CH₂CHF₂(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₂CHF₂ CH₃(S) G²-2 Cl H CF₃H — CH₂CHF₂(Z) H G²-2 Cl H CH═NOCH₃ H — CH₂CHF₂ H G²-2 Cl H CH═NOEt H —CH₂CHF₂ H G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CHF₂ CH₃ G²-2 Cl H C(CH₃)═NOCH₃H — CH₂CHF₂ CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CHF₂ H G²-2 Cl HC(CH₃)═NOEt H — CH₂CHF₂ H G²-2 Cl H C(Et)═NOCH₃ H — CH₂CHF₂ H G²-2 Cl HC≡CH H — CH₂CHF₂ H G²-2 Cl H C≡CH H — CH₂CHF₂(Z) H G²-2 Cl H C≡CCH₃ H —CH₂CHF₂ H G²-2 Cl H C≡CCH₃ H — CH₂CHF₂(Z) H G²-2 Cl H C≡CEt H — CH₂CHF₂H G²-2 Cl H C≡CPr-n H — CH₂CHF₂ H G²-2 Cl H C≡CPr-c H — CH₂CHF₂ H G²-2Cl H C≡CPr-c H — CH₂CHF₂(Z) CH₃ G²-2 Cl H C≡CPr-c H — CH₂CHF₂ CH₃ G²-2Cl H C≡CPr-c H — CH₂CHF₂(Z) CH₃(S) G²-2 Cl H C≡CPr-c H — CH₂CHF₂ CH₃(S)G²-2 Cl H C≡CPr-c H — CH₂CHF₂(Z) H G²-2 Cl H C≡CBu-n H — CH₂CHF₂ H G²-2Cl H C≡CBu-t H — CH₂CHF₂ H G²-2 Cl H C≡CBu-t H — CH₂CHF₂(Z) CH₃ G²-2 ClH C≡CBu-t H — CH₂CHF₂ CH₃ G²-2 Cl H C≡CBu-t H — CH₂CHF₂(Z) CH₃(S) G²-2Cl H C≡CBu-t H — CH₂CHF₂ CH₃(S) G²-2 Cl H C≡CBu-t H — CH₂CHF₂(Z) H G²-2Cl H C≡CPen-c H — CH₂CHF₂ H G²-2 Cl H C≡CPen-c H — CH₂CHF₂(Z) H G²-2 ClH C≡CCl H — CH₂CHF₂ H G²-2 Cl H C≡CBr H — CH₂CHF₂ H G²-2 Cl H C≡CI H —CH₂CHF₂ H G²-2 Cl H C≡CC(CH₃)₂OH H — CH₂CHF₂ H G²-2 Cl H C≡CC(CH₃)₂OH H— CH₂CHF₂(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂CHF₂ H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — CH₂CHF₂(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂CHF₂ H G²-2Cl H C≡CSi(CH₃)₃ H — CH₂CHF₂(Z) H G²-2 Cl H C≡CPh H — CH₂CHF₂ H G²-2 ClH C≡CPh H — CH₂CHF₂(Z) H G²-2 Cl F Cl H — CH₂CHF₂ H G²-2 Cl F Cl H —CH₂CHF₂(Z) CH₃ G²-2 Cl F Cl H — CH₂CHF₂(Z) CH₃(S) G²-2 Cl F Cl H —CH₂CHF₂(Z) H G²-2 Cl Cl Cl H — CH₂CHF₂ H G²-2 Cl Cl Cl H — CH₂CHF₂(Z)CH₃ G²-2 Cl Cl Cl H — CH₂CHF₂(Z) CH₃(S) G²-2 Cl Cl Cl H — CH₂CHF₂(Z) HG²-2 Br H F H — CH₂CHF₂ H G²-2 Br H F H — CH₂CHF₂(Z) H G²-2 Br H Cl H —CH₂CHF₂ H G²-2 Br H Cl H — CH₂CHF₂(Z) CH₃ G²-2 Br H Cl H — CH₂CHF₂(Z)CH₃(S) G²-2 Br H Cl H — CH₂CHF₂(Z) H G²-2 Br H Br H — CH₂CHF₂ H G²-2 BrH Br H — CH₂CHF₂(Z) CH₃ G²-2 Br H Br H — CH₂CHF₂ CH₃ G²-2 Br H Br H —CH₂CHF₂(Z) CH₃(S) G²-2 Br H Br H — CH₂CHF₂ CH₃(S) G²-2 Br H Br H —CH₂CHF₂(Z) H G²-2 Br H CF₃ H — CH₂CHF₂ H G²-2 Br H CF₃ H — CH₂CHF₂(Z) HG²-6 Cl — Cl H — CH₂CHF₂ CH₃ G²-6 Cl — Cl H — CH₂CHF₂ CH₃ G²-9 Cl H Cl —— CH₂CHF₂ CH₃ G²-9 Cl H Cl — — CH₂CHF₂(Z) CH₃ G²-9 Cl H Br — — CH₂CHF₂CH₃ G²-9 Cl H Br — — CH₂CHF₂(Z) CH₃ G²-9 Cl H C≡CPr-c — — CH₂CHF₂ CH₃G²-9 Cl H C≡CPr-c — — CH₂CHF₂(Z) CH₃ G²-9 Cl H C≡CBu-t — — CH₂CHF₂ CH₃G²-9 Cl H C≡CBu-t — — CH₂CHF₂(Z) CH₃ G²-9 Cl Cl Cl — — CH₂CHF₂ CH₃ G²-9Cl Cl Cl — — CH₂CHF₂(Z) CH₃ G²-1 H H CF₃ H H CH₂CF₃ CH₃ G²-1 H H OPh H HCH₂CF₃ CH₃ G²-1 H H Ph H H CH₂CF₃ CH₃ G²-1 H F F F H CH₂CF₃ CH₃ G²-1 H—CH═CHCH═CH— H H CH₂CF₃ CH₃ G²-1 F H Br H H CH₂CF₃ CH₃ G²-1 Cl H F H HCH₂CF₃ CH₃ G²-1 Cl H F H H CH₂CF₃(E) CH₃(S) G²-1 Cl H F H H CH₂CF₃CH₃(S) G²-1 Cl H F H H CH₂CF₃(E) CH₃ G²-1 Cl H Cl H H CH₂CF₃ CH₃ G²-1 ClH Br H H CH₂CF₃ H G²-2 F H Cl H — CH₂CF₃ H G²-2 F H Cl H — CH₂CF₃(Z) CH₃G²-2 F H Cl H — CH₂CF₃(Z) CH₃(S) G²-2 F H Cl H — CH₂CF₃(Z) H G²-2 F H BrH — CH₂CF₃ H G²-2 F H Br H — CH₂CF₃(Z) CH₃ G²-2 F H Br H — CH₂CF₃(Z)CH₃(S) G²-2 F H Br H — CH₂CF₃(Z) H G²-2 F H CF₃ H — CH₂CF₃ H G²-2 F HCF₃ H — CH₂CF₃(Z) H G²-2 Cl H F H — CH₂CF₃ H G²-2 Cl H F H — CH₂CF₃(Z)CH₃ G²-2 Cl H F H — CH₂CF₃(Z) CH₃(S) G²-2 Cl H F H — CH₂CF₃(Z) H G²-2 ClH Cl H — CH₂CF₃ H G²-2 Cl H Cl H — CH₂CF₃(E) H G²-2 Cl H Cl H —CH₂CF₃(Z) CH₃ G²-2 Cl H Cl H — CH₂CF₃ CH₃ G²-2 Cl H Cl H — CH₂CF₃(Z)CH₃(S) G²-2 Cl H Cl H — CH₂CF₃ CH₃(S) G²-2 Cl H Cl H — CH₂CF₃(Z) H G²-2Cl H Cl F — CH₂CF₃ H G²-2 Cl H Cl F — CH₂CF₃(Z) CH₃ G²-2 Cl H Cl F —CH₂CF₃ CH₃ G²-2 Cl H Cl F — CH₂CF₃(Z) CH₃(S) G²-2 Cl H Cl F — CH₂CF₃CH₃(S) G²-2 Cl H Cl F — CH₂CF₃(Z) H G²-2 Cl H Cl Cl — CH₂CF₃ H G²-2 Cl HCl Cl — CH₂CF₃(Z) H G²-2 Cl H Br H — CH₂CF₃ H G²-2 Cl H Br H — CH₂CF₃(Z)CH₃ G²-2 Cl H Br H — CH₂CF₃ CH₃ G²-2 Cl H Br H — CH₂CF₃(Z) CH₃(S) G²-2Cl H Br H — CH₂CF₃ CH₃(S) G²-2 Cl H Br H — CH₂CF₃(Z) H G²-2 Cl H CF₃ H —CH₂CF₃ H G²-2 Cl H CF₃ H — CH₂CF₃(Z) CH₃ G²-2 Cl H CF₃ H — CH₂CF₃ CH₃G²-2 Cl H CF₃ H — CH₂CF₃(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₂CF₃ CH₃(S) G²-2Cl H CF₃ H — CH₂CF₃(Z) H G²-2 Cl H CH═NOCH₃ H — CH₂CF₃ H G²-2 Cl HCH═NOEt H — CH₂CF₃ H G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CF₃ CH₃ G²-2 Cl HC(CH₃)═NOCH₃ H — CH₂CF₃ CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CF₃ H G²-2Cl H C(CH₃)═NOEt H — CH₂CF₃ H G²-2 Cl H C(Et)═NOCH₃ H — CH₂CF₃ H G²-2 ClH C≡CH H — CH₂CF₃ H G²-2 Cl H C≡CH H — CH₂CF₃(Z) H G²-2 Cl H C≡CCH₃ H —CH₂CF₃ H G²-2 Cl H C≡CCH₃ H — CH₂CF₃(Z) H G²-2 Cl H C≡CEt H — CH₂CF₃ HG²-2 Cl H C≡CPr-n H — CH₂CF₃ H G²-2 Cl H C≡CPr-c H — CH₂CF₃ H G²-2 Cl HC≡CPr-c H — CH₂CF₃(Z) CH₃ G²-2 Cl H C≡CPr-c H — CH₂CF₃ CH₃ G²-2 Cl HC≡CPr-c H — CH₂CF₃(Z) CH₃(S) G²-2 Cl H C≡CPr-c H — CH₂CF₃ CH₃(S) G²-2 ClH C≡CPr-c H — CH₂CF₃(Z) H G²-2 Cl H C≡CBu-n H — CH₂CF₃ H G²-2 Cl HC≡CBu-t H — CH₂CF₃ H G²-2 Cl H C≡CBu-t H — CH₂CF₃(Z) CH₃ G²-2 Cl HC≡CBu-t H — CH₂CF₃ CH₃ G²-2 Cl H C≡CBu-t H — CH₂CF₃(Z) CH₃(S) G²-2 Cl HC≡CBu-t H — CH₂CF₃ CH₃(S) G²-2 Cl H C≡CBu-t H — CH₂CF₃(Z) H G²-2 Cl HC≡CPen-c H — CH₂CF₃ H G²-2 Cl H C≡CPen-c H — CH₂CF₃(Z) H G²-2 Cl H C≡CClH — CH₂CF₃ H G²-2 Cl H C≡CBr H — CH₂CF₃ H G²-2 Cl H C≡CI H — CH₂CF₃ HG²-2 Cl H C≡CC(CH₃)₂OH H — CH₂CF₃ H G²-2 Cl H C≡CC(CH₃)₂OH H — CH₂CF₃(Z)H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂CF₃ H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH₂CF₃(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂CF₃ H G²-2 Cl H C≡CSi(CH₃)₃ H —CH₂CF₃(Z) H G²-2 Cl H C≡CPh H — CH₂CF₃ H G²-2 Cl H C≡CPh H — CH₂CF₃(Z) HG²-2 Cl F Cl H — CH₂CF₃ H G²-2 Cl F Cl H — CH₂CF₃(Z) CH₃ G²-2 Cl F Cl H— CH₂CF₃(Z) CH₃(S) G²-2 Cl F Cl H — CH₂CF₃(Z) H G²-2 Cl Cl Cl H — CH₂CF₃H G²-2 Cl Cl Cl H — CH₂CF₃(Z) CH₃ G²-2 Cl Cl Cl H — CH₂CF₃(Z) CH₃(S)G²-2 Cl Cl Cl H — CH₂CF₃(Z) H G²-2 Br H F H — CH₂CF₃ H G²-2 Br H F H —CH₂CF₃(Z) H G²-2 Br H Cl H — CH₂CF₃ H G²-2 Br H Cl H — CH₂CF₃(Z) CH₃G²-2 Br H Cl H — CH₂CF₃(Z) CH₃(S) G²-2 Br H Cl H — CH₂CF₃(Z) H G²-2 Br HBr H — CH₂CF₃ H G²-2 Br H Br H — CH₂CF₃(Z) CH₃ G²-2 Br H Br H — CH₂CF₃CH₃ G²-2 Br H Br H — CH₂CF₃(Z) CH₃(S) G²-2 Br H Br H — CH₂CF₃ CH₃(S)G²-2 Br H Br H — CH₂CF₃(Z) H G²-2 Br H CF₃ H — CH₂CF₃ H G²-2 Br H CF₃ H— CH₂CF₃(Z) H G²-6 Cl — Cl H — CH₂CF₃ CH₃ G²-6 Cl — Cl H — CH₂CF₃ CH₃G²-9 Cl H Cl — — CH₂CF₃ CH₃ G²-9 Cl H Cl — — CH₂CF₃(Z) CH₃ G²-9 Cl H Br— — CH₂CF₃ CH₃ G²-9 Cl H Br — — CH₂CF₃(Z) CH₃ G²-9 Cl H C≡CPr-c — —CH₂CF₃ CH₃ G²-9 Cl H C≡CPr-c — — CH₂CF₃(Z) CH₃ G²-9 Cl H C≡CBu-t — —CH₂CF₃ CH₃ G²-9 Cl H C≡CBu-t — — CH₂CF₃(Z) CH₃ G²-9 Cl Cl Cl — — CH₂CF₃CH₃ G²-9 Cl Cl Cl — — CH₂CF₃(Z) H G²-2 Cl H Cl H — CF₂CHF₂ H G²-2 Cl HCl H — CF₂CHF₂(Z) H G²-2 Cl H Cl H — CH₂CF₂Cl H G²-2 Cl H Cl H —CH₂CF₂Cl(Z) H G²-2 Cl H CF₃ H — CH₂CF₂Cl H G²-2 Cl H CF₃ H — CH₂CF₂Cl(Z)H G²-2 Cl H Cl H — CH₂CF₂CH₃ H G²-2 Cl H Cl H — CH₂CF₂CH₃(Z) H G²-2 Cl HCF₃ H — CH₂CF₂CH₃ H G²-2 Cl H CF₃ H — CH₂CF₂CH₃(Z) H G²-2 Cl H Cl H —CH₂CH₂CF₃ H G²-2 Cl H Cl H — CH₂CH₂CF₃(Z) H G²-2 Cl H CF₃ H — CH₂CH₂CF₃H G²-2 Cl H CF₃ H — CH₂CH₂CF₃(Z) H G²-2 Cl H Cl H — CH(CH₃)CF₃ H G²-2 ClH Cl H — CH(CH₃)CF₃(Z) H G²-2 Cl H CF₃ H — CH(CH₃)CF₃ H G²-2 Cl H CF₃ H— CH(CH₃)CF₃(Z) H G²-2 Cl H Cl H — CH₂CF₂CHF₂ H G²-2 Cl H Cl H —CH₂CF₂CHF₂(Z) H G²-2 Cl H CF₃ H — CH₂CF₂CHF₂ H G²-2 Cl H CF₃ H —CH₂CF₂CHF₂(Z) H G²-2 Cl H Cl H — CH₂CF₂CF₃ H G²-2 Cl H Cl H —CH₂CF₂CF₃(Z) H G²-2 Cl H Cl H — CF₂CHFCF₃ H G²-2 Cl H Cl H —CF₂CHFCF₃(Z) H G²-2 Cl H Cl H — CH(CF₃)₂ H G²-2 Cl H Cl H — CH(CF₃)₂(Z)H G²-2 Cl H Cl H — CH₂(T-1) H G²-2 Cl H Cl H — CH₂(T-2) H G²-2 Cl H Cl H— T-2 H G²-2 Cl H Cl H — CH(CH₃)OEt H G²-2 Cl H Cl H — CH(CH₃)OEt(Z) HG²-2 Cl H CF₃ H — CH(CH₃)OEt H G²-2 Cl H CF₃ H — CH(CH₃)OEt(Z) H G²-2 ClH Cl H — CH(CH₃)OCH₂CF₃ H G²-2 Cl H CF₃ H — E-5-1a H G²-2 Cl H Cl H —E-14-1a CH₃ G²-1 Cl H Cl H H CH₂CH₂OCH₃ CH₃ G²-1 Br H F H H CH₂CH₂OCH₃ HG²-2 Cl H Cl H — CH₂CH₂OCH₃ H G²-2 Cl H CF₃ H — CH₂CH₂OCH₃(Z) H G²-2 ClH CF₃ H — CH₂(E-2-1a) H G²-2 Cl H Cl H — CH₂(E-5-1a) H G²-2 Cl H Cl H —CH₂(E-9-1a) H G²-2 Cl H Cl H — E-2-2a H G²-2 Cl H CF₃ H — E-5-2a H G²-2Cl H CF₃ H — E-14-2a H G²-2 Cl H CF₃ H — CH₂(E-2-2a) H G²-2 Cl H Cl H —CH₂(E-5-2a) H G²-2 Cl H CF₃ H — E-14-3a H G²-2 Cl H Cl H — CH₂CH₂OCH₂CF₃H G²-2 Cl H Cl H — CF₂CHFOCF₂CF₂CF₃ H G²-2 Cl H Cl H — CH₂CH₂SCH₃ H G²-2Cl H Cl H — CH₂CH₂SCH₃(Z) H G²-2 Cl H CF₃ H — CH₂CH₂SCH₃ H G²-2 Cl H CF₃H — CH₂CH₂SCH₃(Z) H G²-2 Cl H CF₃ H — E-3-2a H G²-2 Cl H CF₃ H — E-3-2bH G²-2 Cl H CF₃ H — E-3-2c H G²-2 Cl H CF₃ H — E-6-2a H G²-2 Cl H CF₃ H— E-6-2b H G²-2 Cl H CF₃ H — E-6-2c H G²-2 Cl H CF₃ H — CH₂(E-6-1a) HG²-2 Cl H CF₃ H — CH₂(E-6-1b) H G²-2 Cl H CF₃ H — CH₂(E-6-1c) H G²-2 ClH CF₃ H — CH₂(E-6-2a) H G²-2 Cl H CF₃ H — CH₂(E-6-2b) H G²-2 Cl H CF₃ H— CH₂(E-6-2c) H G²-2 Cl H CF₃ H — E-15-2a H G²-2 Cl H CF₃ H — E-15-2b HG²-2 Cl H CF₃ H — E-15-2c H G²-2 Cl H CF₃ H — E-15-3a H G²-2 Cl H CF₃ H— E-15-3b H G²-2 Cl H CF₃ H — E-15-3c H G²-2 Cl H CF₃ H — (E-4-2a)CHO HG²-2 Cl H CF₃ H — (E-4-2a)C(O)CH₃ H G²-2 Cl H CF₃ H — (E-4-2a)C(O)OCH₃ HG²-2 Cl H CF₃ H — CH₂(E-4-1a)CHO H G²-2 Cl H CF₃ H — CH₂(E-4-1a)C(O)CH₃H G²-2 Cl H CF₃ H — CH₂(E-4-1a)C(O)OCH₃ H G²-2 Cl H CF₃ H —CH₂(E-4-2a)CHO H G²-2 Cl H CF₃ H — CH₂(E-4-2a)C(O)CH₃ H G²-2 Cl H CF₃ H— CH₂(E-4-2a)C(O)OCH₃ H G²-2 Cl H CF₃ H — (E-8-2a)CHO H G²-2 Cl H CF₃ H— (E-8-2a)C(O)CH₃ H G²-2 Cl H CF₃ H — (E-8-2a)C(O)OCH₃ H G²-2 Cl H CF₃ H— CH₂(E-8-1a)CHO H G²-2 Cl H CF₃ H — CH₂(E-8-1a)C(O)CH₃ H G²-2 Cl H CF₃H — CH₂(E-8-1a)C(O)OCH₃ H G²-2 Cl H CF₃ H — CH₂(E-8-2a)CHO H G²-2 Cl HCF₃ H — CH₂(E-8-2a)C(O)CH₃ H G²-2 Cl H CF₃ H — CH₂(E-8-2a)C(O)OCH₃ HG²-2 Cl H CF₃ H — (E-17-2a)CHO H G²-2 Cl H CF₃ H — (E-17-2a)C(O)CH₃ HG²-2 Cl H CF₃ H — (E-17-2a)C(O)OCH₃ H G²-2 Cl H CF₃ H — (E-17-3a)CHO HG²-2 Cl H CF₃ H — (E-17-3a)C(O)CH₃ H G²-2 Cl H CF₃ H — (E-17-3a)C(O)OCH₃H G²-2 Cl H Cl H — CH₂Si(CH₃)₃ H G²-2 Cl H Cl H — CH₂Si(CH₃)₃(Z) H G²-2Cl H CF₃ H — CH₂Si(CH₃)₃ H G²-2 Cl H CF₃ H — CH₂Si(CH₃)₃(Z) H G²-2 Cl HCl H — CH₂C(CH₃)═NOCH₃ H G²-2 Cl H CF₃ H — CH₂C(CH₃)═NOCH₃ H G²-2 Cl HCF₃ H — CH₂(M-3-b)CH₃ H G²-2 Cl H CF₃ H — CH₂(M-4-2a)CH₃ H G²-2 Cl H ClH — CH₂CN H G²-2 Cl H CF₃ H — CH₂CN H G²-2 Cl H Cl H — CH(CH₃)CN H G²-2Cl H CF₃ H — CH(CH₃)CN H G²-2 Cl H CF₃ H — CH₂CH₂CN H G²-2 Cl H Cl H —CH₂C(O)OCH₃ H G²-2 Cl H Cl H — CH₂C(O)OEt H G²-2 Cl H CF₃ H — CH₂C(O)NH₂H G²-2 Cl H CF₃ H — CH₂C(O)NHCH₂CF₃ H G²-2 Cl H CF₃ H — CH₂C(S)NH₂ CH₃G²-1 Cl H F H H CH₂CH═CH₂ CH₃ G²-1 Cl H F H H CH₂CH═CH₂(E) CH₃(S) G²-1Cl H F H H CH₂CH═CH₂ CH₃(S) G²-1 Cl H F H H CH₂CH═CH₂(E) H G²-2 F H Cl H— CH₂CH═CH₂ H G²-2 F H Cl H — CH₂CH═CH₂(Z) CH₃ G²-2 F H Cl H —CH₂CH═CH₂(Z) CH₃(S) G²-2 F H Cl H — CH₂CH═CH₂(Z) H G²-2 F H Br H —CH₂CH═CH₂ H G²-2 F H Br H — CH₂CH═CH₂(Z) CH₃ G²-2 F H Br H —CH₂CH═CH₂(Z) CH₃(S) G²-2 F H Br H — CH₂CH═CH₂(Z) H G²-2 F H CF₃ H —CH₂CH═CH₂ H G²-2 F H CF₃ H — CH₂CH═CH₂(Z) H G²-2 Cl H F H — CH₂CH═CH₂ HG²-2 Cl H F H — CH₂CH═CH₂(Z) CH₃ G²-2 Cl H F H — CH₂CH═CH₂(Z) CH₃(S)G²-2 Cl H F H — CH₂CH═CH₂(Z) H G²-2 Cl H Cl H — CH₂CH═CH₂ H G²-2 Cl H ClH — CH₂CH═CH₂(Z) CH₃ G²-2 Cl H Cl H — CH₂CH═CH₂ CH₃ G²-2 Cl H Cl H —CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl H Cl H — CH₂CH═CH₂ CH₃(S) G²-2 Cl H Cl H —CH₂CH═CH₂(Z) H G²-2 Cl H Cl F — CH₂CH═CH₂ H G²-2 Cl H Cl F —CH₂CH═CH₂(Z) CH₃ G²-2 Cl H Cl F — CH₂CH═CH₂ CH₃ G²-2 Cl H Cl F —CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl H Cl F — CH₂CH═CH₂ CH₃(S) G²-2 Cl H Cl P —CH₂CH═CH₂(Z) H G²-2 Cl H Cl Cl — CH₂CH═CH₂ H G²-2 Cl H Cl Cl —CH₂CH═CH₂(Z) H G²-2 Cl H Br H — CH₂CH═CH₂ H G²-2 Cl H Br H —CH₂CH═CH₂(Z) CH₃ G²-2 Cl H Br H — CH₂CH═CH₂ CH₃ G²-2 Cl H Br H —CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl H Br H — CH₂CH═CH₂ CH₃(S) G²-2 Cl H Br H —CH₂CH═CH₂(Z) H G²-2 Cl H CF₃ H — CH₂CH═CH₂ H G²-2 Cl H CF₃ H —CH₂CH═CH₂(Z) CH₃ G²-2 Cl H CF₃ H — CH₂CH═CH₂ CH₃ G²-2 Cl H CF₃ H —CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₂CH═CH₂ CH₃(S) G²-2 Cl H CF₃ H —CH₂CH═CH₂(Z) H G²-2 Cl H CH═NOCH₃ H — CH₂CH═CH₂ H G²-2 Cl H CH═NOEt H —CH₂CH═CH₂ H G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CH═CH₂ CH₃ G²-2 Cl HC(CH₃)═NOCH₃ H — CH₂CH═CH₂ CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — CH₂CH═CH₂ HG²-2 Cl H C(CH₃)═NOEt H — CH₂CH═CH₂ H G²-2 Cl H C(Et)═NOCH₃ H —CH₂CH═CH₂ H G²-2 Cl H C≡CH H — CH₂CH═CH₂ H G²-2 Cl H C≡CH H —CH₂CH═CH₂(Z) H G²-2 Cl H C≡CPr-c H — CH₂CH═CH₂ H G²-2 Cl H C≡CPr-c H —CH₂CH═CH₂(Z) H G²-2 Cl H C≡CBu-t H — CH₂CH═CH₂ H G²-2 Cl H C≡CBu-t H —CH₂CH═CH₂(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂CH═CH₂ H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — CH₂CH═CH₂(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂CH═CH₂ HG²-2 Cl H C≡CSi(CH₃)₃ H — CH₂CH═CH₂(Z) H G²-2 Cl H C≡CPh H — CH₂CH═CH₂ HG²-2 Cl H C≡CPh H — CH₂CH═CH₂(Z) H G²-2 Cl F Cl H — CH₂CH═CH₂ H G²-2 ClF Cl H — CH₂CH═CH₂(Z) CH₃ G²-2 Cl F Cl H — CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl FCl H — CH₂CH═CH₂(Z) H G²-2 Cl Cl Cl H — CH₂CH═CH₂ H G²-2 Cl Cl Cl H —CH₂CH═CH₂(Z) CH₃ G²-2 Cl Cl Cl H — CH₂CH═CH₂(Z) CH₃(S) G²-2 Cl Cl Cl H —CH₂CH═CH₂(Z) H G²-2 Br H F H — CH₂CH═CH₂ H G²-2 Br H F H — CH₂CH═CH₂(Z)H G²-2 Br H Cl H — CH₂CH═CH₂ H G²-2 Br H Cl H — CH₂CH═CH₂(Z) CH₃ G²-2 BrH Cl H — CH₂CH═CH₂(Z) CH₃(S) G²-2 Br H Cl H — CH₂CH═CH₂(Z) H G²-2 Br HBr H — CH₂CH═CH₂ H G²-2 Br H Br H — CH₂CH═CH₂(Z) CH₃ G²-2 Br H Br H —CH₂CH═CH₂ CH₃ G²-2 Br H Br H — CH₂CH═CH₂(Z) CH₃(S) G²-2 Br H Br H —CH₂CH═CH₂ CH₃(S) G²-2 Br H Br H — CH₂CH═CH₂(Z) H G²-2 Br H CF₃ H —CH₂CH═CH₂ H G²-2 Br H CF₃ H — CH₂CH═CH₂(Z) H G²-2 Cl H Cl H —CH₂C(CH₃)═CH₂ H G²-2 Cl H Cl H — CH₂C(CH₃)═CH₂(Z) H G²-2 Cl H CF₃ H —CH₂C(CH₃)═CH₂ H G²-2 Cl H CF₃ H — CH₂C(CH₃)═CH₂(Z) CH₃ G²-1 Cl H F H HCH(CH₃)CH═CH₂ CH₃ G²-1 Cl H F H H CH(CH₃)CH═CH₂(E) CH₃(S) G²-1 Cl H F HH CH(CH₃)CH═CH₂ CH₃(S) G²-1 Cl H F H H CH(CH₃)CH═CH₂(E) H G²-2 F H Cl H— CH(CH₃)CH═CH₂ H G²-2 F H Cl H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 F H Cl H —CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 F H Cl H — CH(CH₃)CH═CH₂(Z) H G²-2 F H Br H— CH(CH₃)CH═CH₂ H G²-2 F H Br H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 F H Br H —CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 F H Br H — CH(CH₃)CH═CH₂(Z) H G²-2 F H CF₃H — CH(CH₃)CH═CH₂ H G²-2 F H CF₃ H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl H F H —CH(CH₃)CH═CH₂ H G²-2 Cl H F H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl H F H — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 Cl H F H — CH (CH₃)CH═CH₂(Z) H G²-2 Cl H Cl H— CH(CH₃)CH═CH₂ H G²-2 Cl H Cl H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl H Cl H —CH(CH₃)CH═CH₂ CH₃ G²-2 Cl H Cl H — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 Cl H ClH — CH(CH₃)CH═CH₂ CH₃(S) G²-2 Cl H Cl H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl HCl F — CH(CH₃)CH═CH₂ H G²-2 Cl H Cl F — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl HCl F — CH(CH₃)CH═CH₂ CH₃ G²-2 Cl H Cl F — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2Cl H Cl F — CH(CH₃)CH═CH₂ CH₃(S) G²-2 Cl H Cl F — CH(CH₃)CH═CH₂(Z) HG²-2 Cl H Cl Cl — CH(CH₃)CH═CH₂ H G²-2 Cl H Cl Cl — CH(CH₃)CH═CH₂(Z) HG²-2 Cl H Br H — CH(CH₃)CH═CH₂ H G²-2 Cl H Br H — CH(CH₃)CH═CH₂(Z) CH₃G²-2 Cl H Br H — CH(CH₃)CH═CH₂ CH₃ G²-2 Cl H Br H — CH(CH₃)CH═CH₂(Z)CH₃(S) G²-2 Cl H Br H — CH(CH₃)CH═CH₂ CH₃(S) G²-2 Cl H Br H —CH(CH₃)CH═CH₂(Z) H G²-2 Cl H CF₃ H — CH(CH₃)CH═CH₂ H G²-2 Cl H CF₃ H —CH(CH₃)CH═CH₂(E) H G²-2 Cl H CF₃ H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl H CF₃H — CH(CH₃)CH═CH₂ CH₃ G²-2 Cl H CF₃ H — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 ClH CF₃ H — CH(CH₃)CH═CH₂ CH₃(S) G²-2 Cl H CF₃ H — CH(CH₃)CH═CH₂(Z) H G²-2Cl H CH═NOCH₃ H — CH(CH₃)CH═CH₂ H G²-2 Cl H CH═NOEt H — CH(CH₃)CH═CH₂ HG²-2 Cl H C(CH₃)═NOCH₃ H — CH(CH₃)CH═CH₂ CH₃ G²-2 Cl H C(CH₃)═NOCH₃ H —CH(CH₃)CH═CH₂ CH₃(S) G²-2 Cl H C(CH₃)═NOCH₃ H — CH(CH₃)CH═CH₂ H G²-2 ClH C(CH₃)═NOEt H — CH(CH₃)CH═CH₂ H G²-2 Cl H C(Et)═NOCH₃ H —CH(CH₃)CH═CH₂ H G²-2 Cl H C≡CH H — CH(CH₃)CH═CH₂ H G²-2 Cl H C≡CH H —CH(CH₃)CH═CH₂(Z) H G²-2 Cl H C≡CPr-c H — CH(CH₃)CH═CH₂ H G²-2 Cl HC≡CPr-c H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl H C≡CBu-t H — CH(CH₃)CH═CH₂ HG²-2 Cl H C≡CBu-t H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH(CH₃)CH═CH₂ H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH(CH₃)CH═CH₂(Z) H G²-2 ClH C≡CSi(CH₃)₃ H — CH(CH₃)CH═CH₂ H G²-2 Cl H C≡CSi(CH₃)₃ H —CH(CH₃)CH═CH₂(Z) H G²-2 Cl H C≡CPh H — CH(CH₃)CH═CH₂ H G²-2 Cl H C≡CPh H— CH(CH₃)CH═CH₂(Z) H G²-2 Cl F Cl H — CH(CH₃)CH═CH₂ H G²-2 Cl F Cl H —CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl F Cl H — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 Cl FCl H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl Cl Cl H — CH(CH₃)CH═CH₂ H G²-2 Cl ClCl H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Cl Cl Cl H — CH(CH₃)CH═CH₂(Z) CH₃(S)G²-2 Cl Cl Cl H — CH(CH₃)CH═CH₂(Z) H G²-2 Br H F H — CH(CH₃)CH═CH₂ HG²-2 Br H F H — CH(CH₃)CH═CH₂(Z) H G²-2 Br H Cl H — CH(CH₃)CH═CH₂ H G²-2Br H Cl H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Br H Cl H — CH(CH₃)CH═CH₂(Z)CH₃(S) G²-2 Br H Cl H — CH(CH₃)CH═CH₂(Z) H G²-2 Br H Br H —CH(CH₃)CH═CH₂ H G²-2 Br H Br H — CH(CH₃)CH═CH₂(Z) CH₃ G²-2 Br H Br H —CH(CH₃)CH═CH₂ CH₃ G²-2 Br H Br H — CH(CH₃)CH═CH₂(Z) CH₃(S) G²-2 Br H BrH — CH(CH₃)CH═CH₂ CH₃(S) G²-2 Br H Br H — CH(CH₃)CH═CH₂(Z) H G²-2 Br HCF₃ H — CH(CH₃)CH═CH₂ H G²-2 Br H CF₃ H — CH(CH₃)CH═CH₂(Z) H G²-2 Cl HCF₃ H — CH₂CH═C(CH₃)₂ H G²-2 Cl H Cl H — CH₂CF═CH₂ H G²-2 Cl H Cl H —CH₂CF═CH₂(Z) H G²-2 Cl H CF₃ H — CH₂CF═CH₂ H G²-2 Cl H CF₃ H —CH₂CF═CH₂(Z) H G²-2 Cl H Cl H — CH₂CCl═CH₂ H G²-2 Cl H Cl H —CH₂CCl═CH₂(Z) CH₃ G²-2 Cl H Cl H — CH₂CCl═CH₂(Z) CH₃(S) G²-2 Cl H Cl H —CH₂CCl═CH₂(Z) H G²-2 Cl H Cl F — CH₂CCl═CH₂ H G²-2 Cl H Cl F —CH₂CCl═CH₂(Z) H G²-2 Cl H Br H — CH₂CCl═CH₂ H G²-2 Cl H Br H —CH₂CCl═CH₂(Z) CH₃ G²-2 Cl H Br H — CH₂CCl═CH₂(Z) CH₃(S) G²-2 Cl H Br H —CH₂CCl═CH₂(Z) H G²-2 Cl H CF₃ H — CH₂CCl═CH₂ H G²-2 Cl H CF₃ H —CH₂CCl═CH₂(Z) CH₃ G²-2 Cl H CF₃ H — CH₂CCl═CH₂(Z) CH₃(S) G²-2 Cl H CF₃ H— CH₂CCl═CH₂(Z) H G²-2 Cl H C≡CPr-c H — CH₂CCl═CH₂ H G²-2 Cl H C≡CPr-c H— CH₂CCl═CH₂(Z) H G²-2 Cl H C≡CBu-t H — CH₂CCl═CH₂ H G²-2 Cl H C≡CBu-t H— CH₂CCl═CH₂(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂CCl═CH₂ H G²-2 Cl HC≡CC(CH₃)₂OCH₃ H — CH₂CCl═CH₂(Z) H G²-2 Cl H G≡CSi(CH₃)₃ H — CH₂CCl═CH₂H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂CCl═CH₂(Z) H G²-2 Cl H C≡CPh H —CH₂CCl═CH₂ H G²-2 Cl H C≡CPh H — CH₂CCl═CH₂(Z) H G²-2 Cl F Cl H —CH₂CCl═CH₂ H G²-2 Cl F Cl H — CH₂CCl═CH₂(Z) H G²-2 Br H Cl H —CH₂CCl═CH₂ H G²-2 Br H Cl H — CH₂CCl═CH₂(Z) H G²-2 Br H Br H —CH₂CCl═CH₂ H G²-2 Br H Br H — CH₂CCl═CH₂(Z) H G²-2 Cl H Cl H — CH₂CH═CF₂H G²-2 Cl H Cl H — CH₂CH═CF₂(Z) H G²-2 Cl H CF₃ H — CH₂CH═CF₂ H G²-2 ClH CF₃ H — CH₂CH═CF₂(Z) H G²-2 Cl H Cl H — CH₂CCl═CHCl H G²-2 Cl H Cl H —CH₂CCl═CHCl(Z) H G²-2 Cl H CF₃ H — CH₂CCl═CHCl H G²-2 Cl H CF₃ H —CH₂CCl═CHCl(Z) H G²-2 Cl H Cl H — CH₂CF═CF₂ H G²-2 Cl H Cl H —CH₂CF═CF₂(Z) H G²-2 Cl H CF₃ H — CH₂CF═CF₂ H G²-2 Cl H CF₃ H —CH₂CF═CF₂(Z) H G²-2 Cl H Cl H — CH₂CCl═CF₂ H G²-2 Cl H CF₃ H —CH₂CCl═CF₂ H G²-2 Cl H Cl H — CH₂CH₂CH═CF₂ H G²-2 Cl H CF₃ H —CH₂CH₂CH═CF₂ H G²-2 Cl H Cl H — CH₂CH₂CF═CF₂ H G²-2 Cl H CF₃ H —CH₂CH₂CF═CF₂ H G²-2 Cl H Cl H — CH₂CF═CHCF₃ H G²-2 Cl H CF₃ H —CH₂CF═CHCF₃ H G²-2 Cl H Cl H — CH₂C═CH H G²-2 Cl H Cl H — CH₂C═CH(Z) CH₃G²-2 Cl H Cl H — CH₂C═CH(Z) CH₃(S) G²-2 Cl H Cl H — CH₂C═CH(Z) H G²-2 ClH Cl F — CH₂C═CH H G²-2 Cl H Cl F — CH₂C═CH(Z) H G²-2 Cl H Br H —CH₂C═CH H G²-2 Cl H Br H — CH₂C═CH(Z) CH₃ G²-2 Cl H Br H — CH₂C═CH(Z)CH₃(S) G²-2 Cl H Br H — CH₂C═CH(Z) H G²-2 Cl H CF₃ H — CH₂C═CH H G²-2 ClH CF₃ H — CH₂C═CH(Z) CH₃ G²-2 Cl H CF₃ H — CH₂C≡CH(Z) CH₃(S) G²-2 Cl HCF₃ H — CH₂C≡CH(Z) H G²-2 Cl F Cl H — CH₂C≡CH H G²-2 Cl F Cl H —CH₂C≡CH(Z) H G²-2 Br H Cl H — CH₂C≡CH H G²-2 Br H Cl H — CH₂C≡CH(Z) HG²-2 Br H Br H — CH₂C≡CH H G²-2 Br H Br H — CH₂C≡CH(Z) H G²-2 Cl H Cl H— CH₂C≡CCH₃ H G²-2 Cl H CF₃ H — CH₂C≡CCH₃ H G²-2 Cl H Cl H — CH₂C≡CCl HG²-2 Cl H CF₃ H — CH₂C≡CCl H G²-2 Cl H Cl H — CH₂C≡CBr H G²-2 Cl H CF₃ H— CH₂C≡CBr H G²-2 Cl H Cl H — CH₂C≡CI H G²-2 Cl H CF₃ H — CH₂C≡CI H G²-2Cl H Cl H — CH₂Ph H G²-2 Cl H Cl H — CH₂Ph(Z) H G²-2 Cl H CF₃ H — CH₂PhH G²-2 Cl H CF₃ H — CH₂Ph(Z) H G²-2 Cl H Cl H — CH₂(Ph-2-F) H G²-2 Cl HCl H — CH₂(Ph-2-F)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-2-F) H G²-2 Cl H CF₃ H— CH₂(Ph-2-F)(Z) H G²-2 Cl H Cl H — CH₂(Ph-3-F) H G²-2 Cl H Cl H —CH₂(Ph-3-F)(Z) CH₃ G²-2 Cl H Cl H — CH₂(Ph-3-F)(Z) CH₃(S) G²-2 Cl H Cl H— CH₂(Ph-3-F)(Z) H G²-2 Cl H Cl F — CH₂(Ph-3-F) H G²-2 Cl H Cl F —CH₂(Ph-3-F)(Z) H G²-2 Cl H Br H — CH₂(Ph-3-F) H G²-2 Cl H Br H —CH₂(Ph-3-F)(Z) CH₃ G²-2 Cl H Br H — CH₂(Ph-3-F)(Z) CH₃(S) G²-2 Cl H Br H— CH₂(Ph-3-F)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-3-F) H G²-2 Cl H CF₃ H —CH₂(Ph-3-F)(Z) CH₃ G²-2 Cl H CF₃ H — CH₂(Ph-3-F)(Z) CH₃(S) G²-2 Cl H CF₃H — CH₂(Ph-3-F)(Z) H G²-2 Cl H C≡CPr-c H — CH₂(Ph-3-F) H G²-2 Cl HC≡CPr-c H — CH₂(Ph-3-F)(Z) H G²-2 Cl H C≡CBu-t H — CH₂(Ph-3-F) H G²-2 ClH C≡CBu-t H — CH₂(Ph-3-F)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-3-F)H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-3-F)(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H— CH₂(Ph-3-F) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂(Ph-3-F)(Z) H G²-2 Cl HC≡CPh H — CH₂(Ph-3-F) H G²-2 Cl H C≡CPh H — CH₂(Ph-3-F)(Z) H G²-2 Cl FCl H — CH₂(Ph-3-F) H G²-2 Cl F Cl H — CH₂(Ph-3-F)(Z) H G²-2 Br H Cl H —CH₂(Ph-3-F) H G²-2 Br H Cl H — CH₂(Ph-3-F)(Z) H G²-2 Br H Br H —CH₂(Ph-3-F) H G²-2 Br H Br H — CH₂(Ph-3-F)(Z) H G²-2 Cl H Cl H —CH₂(Ph-4-F) H G²-2 Cl H Cl H — CH₂(Ph-4-F)(Z) CH₃ G²-2 Cl H Cl H —CH₂(Ph-4-F)(Z) CH₃(S) G²-2 Cl H Cl H — CH₂(Ph-4-F)(Z) H G²-2 Cl H Cl F —CH₂(Ph-4-F) H G²-2 Cl H Cl F — CH₂(Ph-4-F)(Z) H G²-2 Cl H Cl Cl —CH₂(Ph-4-F) H G²-2 Cl H Br H — CH₂(Ph-4-F) H G²-2 Cl H Br H —CH₂(Ph-4-F)(Z) CH₃ G²-2 Cl H Br H — CH₂(Ph-4-F)(Z) CH₃(S) G²-2 Cl H Br H— CH₂(Ph-4-F)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-4-F) H G²-2 Cl H CF₃ H —CH₂(Ph-4-F)(Z) CH₃ G²-2 Cl H CF₃ H — CH₂(Ph-4-F)(Z) CH₃(S) G²-2 Cl H CF₃H — CH₂(Ph-4-F)(Z) H G²-2 Cl H C≡CPr-c H — CH₂(Ph-4-F) H G²-2 Cl HC≡CPr-c H — CH₂(Ph-4-F)(Z) H G²-2 Cl H C≡CBu-t H — CH₂(Ph-4-F) H G²-2 ClH C≡CBu-t H — CH₂(Ph-4-F)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-4-F)H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-4-F)(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H— CH₂(Ph-4-F) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂(Ph-4-F)(Z) H G²-2 Cl HC≡CPh H — CH₂(Ph-4-F) H G²-2 Cl H C≡CPh H — CH₂(Ph-4-F)(Z) H G²-2 Cl FCl H — CH₂(Ph-4-F) H G²-2 Cl F Cl H — CH₂(Ph-4-F)(Z) H G²-2 Br H Cl H —CH₂(Ph-4-F) H G²-2 Br H Cl H — CH₂(Ph-4-F)(Z) H G²-2 Br H Br H —CH₂(Ph-4-F) H G²-2 Br H Br H — CH₂(Ph-4-F)(Z) H G²-2 Cl — H Cl HCH₂(Ph-4-F) H G²-2 Cl H Cl H — CH₂(Ph-2-Cl) H G²-2 Cl H CF₃ H —CH₂(Ph-2-Cl) H G²-2 Cl H Cl H — CH₂(Ph-3-Cl) H G²-2 Cl H CF₃ H —CH₂(Ph-3-Cl) CH₃ G²-1 H H F H H CH₂(Ph-4-Cl) CH₃ G²-1 Cl H Cl H HCH₂(Ph-4-Cl) CH₃ G²-1 CH₃ H OPr-i H H CH₂(Ph-4-Cl) H G²-2 Cl H Cl H —CH₂(Ph-4-Cl) H G²-2 Cl H Cl H — CH₂(Ph-4-Cl)(Z) CH₃ G²-2 Cl H Cl H —CH₂(Ph-4-Cl)(Z) CH₃(S) G²-2 Cl H Cl H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl H Cl F— CH₂(Ph-4-Cl) H G²-2 Cl H Cl F — CH₂(Ph-4-Cl)(Z) H G²-2 Cl H Br H —CH₂(Ph-4-Cl) H G²-2 Cl H Br H — CH₂(Ph-4-Cl)(Z) CH₃ G²-2 Cl H Br H —CH₂(Ph-4-Cl)(Z) CH₃(S) G²-2 Cl H Br H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl H CF₃H — CH₂(Ph-4-Cl) H G²-2 Cl H CF₃ H — CH₂(Ph-4-Cl)(Z) CH₃ G²-2 Cl H CF₃ H— CH₂(Ph-4-Cl)(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl HC≡CPr-c H — CH₂(Ph-4-Cl) H G²-2 Cl H C≡CPr-c H — CH₂(Ph-4-Cl)(Z) H G²-2Cl H C≡CBu-t H — CH₂(Ph-4-Cl) H G²-2 Cl H C≡CBu-t H — CH₂(Ph-4-Cl)(Z) HG²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-4-Cl) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH₂(Ph-4-Cl)(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂(Ph-4-Cl) H G²-2 Cl HC≡CSi(CH₃)₃ H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl H C≡CPh H — CH₂(Ph-4-Cl) HG²-2 Cl H C≡CPh H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl F Cl H — CH₂(Ph-4-Cl) HG²-2 Cl F Cl H — CH₂(Ph-4-Cl)(Z) H G²-2 Br H Cl H — CH₂(Ph-4-Cl) H G²-2Br H Cl H — CH₂(Ph-4-Cl)(Z) H G²-2 Br H Br H — CH₂(Ph-4-Cl) H G²-2 Br HBr H — CH₂(Ph-4-Cl)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-2-CH₃) H G²-2 Cl H ClH — CH₂(Ph-3-CH₃) H G²-2 Cl H Cl H — CH₂(Ph-3-CH₃)(Z) H G²-2 Cl H CF₃ H— CH₂(Ph-3-CH₃) H G²-2 Cl H CF₃ H — CH₂(Ph-3-CH₃)(Z) H G²-2 Cl H CF₃ H —CH₂(Ph-4-CH₃) H G²-2 Cl H CF₃ H — CH₂(Ph-4-Bu-t) H G²-2 Cl H CF₃ H —CH₂(Ph-2-CF₃) H G²-2 Cl H Cl H — CH₂(Ph-3-CF₃) H G²-2 Cl H Cl H —CH₂(Ph-3-CF₃)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-3-CF₃) H G²-2 Cl H CF₃ H —CH₂(Ph-3-CF₃)(Z) H G²-2 Cl H Cl H — CH₂(Ph-4-CF₃) H G²-2 Cl H Cl H —CH₂(Ph-4-CF₃)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-4-CF₃) H G²-2 Cl H CF₃ H —CH₂(Ph-4-CF₃)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-3-OCH₃) H G²-2 Cl H Cl H —CH₂(Ph-4-OCH₃) H G²-2 Cl H CF₃ H — CH₂(Ph-4-OCH₃) H G²-2 Cl H CF₃ H —CH₂(Ph-4-OCHF₂) H G²-2 Cl H Cl H — CH₂(Ph-2-OCF₃) H G²-2 Cl H Cl H —CH₂(Ph-2-OCF₃)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-2-OCF₃) H G²-2 Cl H CF₃ H —CH₂(Ph-2-OCF₃)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-3-OCF₃) H G²-2 Cl H CF₃ H —CH₂(Ph-4-OCF₃) H G²-2 Cl H CF₃ H — CH₂(Ph-4-SCH₃) H G²-2 Cl H CF₃ H —CH₂[Ph-4-S(O)CH₃] H G²-2 Cl H CF₃ H — CH₂(Ph-4-SO₂CH₃) H G²-2 Cl H Cl H— CH₂(Ph-4-SCF₃) H G²-2 Cl H CF₃ H — CH₂[Ph-4-S(O)CF₃] H G²-2 Cl H CF₃ H— CH₂(Ph-4-SO₂CF₃) H G²-2 Cl H Cl H — CH₂(Ph-4-NO₂) H G²-2 Cl H Cl H —CH₂(Ph-4-NO₂)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-4-NO₂) H G²-2 Cl H CF₃ H —CH₂(Ph-4-NO₂)(Z) H G²-2 Cl H Cl H — CH₂(Ph-2-CN) H G²-2 Cl H CF₃ H —CH₂(Ph-2-CN) H G²-2 Cl H CF₃ H — CH₂(Ph-3-CN) CH₃ G²-1 Cl H Cl H HCH₂(Ph-4-CN) H G²-2 Cl H Cl H — CH₂(Ph-4-CN) H G²-2 Cl H Cl H —CH₂(Ph-4-CN)(Z) CH₃ G²-2 Cl H Cl H — CH₂(Ph-4-CN)(Z) CH₃(S) G²-2 Cl H ClH — CH₂(Ph-4-CN)(Z) H G²-2 Cl H Cl F — CH₂(Ph-4-CN) H G²-2 Cl H Cl F —CH₂(Ph-4-CN)(Z) H G²-2 Cl H Br H — CH₂(Ph-4-CN) H G²-2 Cl H Br H —CH₂(Ph-4-CN)(Z) CH₃ G²-2 Cl H Br H — CH₂(Ph-4-CN)(Z) CH₃(S) G²-2 Cl H BrH — CH₂(Ph-4-CN)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-4-CN) H G²-2 Cl H CF₃ H —CH₂(Ph-4-CN)(Z) CH₃ G²-2 Cl H CF₃ H — CH₂(Ph-4-CN)(Z) CH₃(S) G²-2 Cl HCF₃ H — CH₂(Ph-4-CN)(Z) H G²-2 Cl H C≡CPr-c H — CH₂(Ph-4-CN) H G²-2 Cl HC≡CPr-c H — CH₂(Ph-4-CN)(Z) H G²-2 Cl H C≡CBu-t H — CH₂(Ph-4-CN) H G²-2Cl H C≡CBu-t H — CH₂(Ph-4-CN)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH₂(Ph-4-CN) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-4-CN)(Z) H G²-2 Cl HC≡CSi(CH₃)₃ H — CH₂(Ph-4-CN) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂(Ph-4-CN)(Z)H G²-2 Cl H C≡CPh H — CH₂(Ph-4-CN) H G²-2 Cl H C≡CPh H — CH₂(Ph-4-CN)(Z)H G²-2 Cl F Cl H — CH₂(Ph-4-CN) H G²-2 Cl F Cl H — CH₂(Ph-4-CN)(Z) HG²-2 Br H Cl H — CH₂(Ph-4-CN) H G²-2 Br H Cl H — CH₂(Ph-4-CN)(Z) H G²-2Br H Br H — CH₂(Ph-4-CN) H G²-2 Br H Br H — CH₂(Ph-4-CN)(Z) H G²-2 Cl HCF₃ H — CH₂(Ph-4-Ph) H G²-2 Cl H CF₃ H — CH₂(Ph-2,4-F₂) H G²-2 Cl H CF₃H — CH₂(Ph-2,6-F₂) H G²-2 Cl H Cl H — CH₂(Ph-3,4-F₂) H G²-2 Cl H Cl H —CH₂(Ph-3,4-F₂)(Z) CH₃ G²-2 Cl H Cl H — CH₂(Ph-3,4-F₂)(Z) CH₃(S) G²-2 ClH Cl H — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl H Cl F — CH₂(Ph-3,4-F₂) H G²-2 Cl HCl F — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl H Br H — CH₂(Ph-3,4-F₂) H G²-2 Cl HBr H — CH₂(Ph-3,4-F₂)(Z) CH₃ G²-2 Cl H Br H — CH₂(Ph-3,4-F₂)(Z) CH₃(S)G²-2 Cl H Br H — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl H CF₃ H — CH₂(Ph-3,4-F₂) HG²-2 Cl H CF₃ H — CH₂(Ph-3,4-F₂)(Z) CH₃ G²-2 Cl H CF₃ H —CH₂(Ph-3,4-F₂)(Z) CH₃(S) G²-2 Cl H CF₃ H — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl HC≡CPr-c H — CH₂(Ph-3,4-F₂) H G²-2 Cl H C≡CPr-c H — CH₂(Ph-3,4-F₂)(Z) HG²-2 Cl H C≡CBu-t H — CH₂(Ph-3,4-F₂) H G²-2 Cl H C≡CBu-t H —CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-3,4-F₂) H G²-2Cl H C≡CC(CH₃)₂OCH₃ H — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl H C≡CSi(CH₃)₃ H —CH₂(Ph-3,4-F₂) H G²-2 Cl H C≡CSi(CH₃)₃ H — CH₂(Ph-3,4-F₂)(Z) H G²-2 Cl HC≡CPh H — CH₂(Ph-3,4-F₂) H G²-2 Cl H C≡CPh H — CH₂(Ph-3,4-F₂)(Z) H G²-2Cl F Cl H — CH₂(Ph-3,4-F₂) H G²-2 Cl F Cl H — CH₂(Ph-3,4-F₂)(Z) H G²-2Br H Cl H — CH₂(Ph-3,4-F₂) H G²-2 Br H Cl H — CH₂(Ph-3,4-F₂)(Z) H G²-2Br H Br H — CH₂(Ph-3,4-F₂) H G²-2 Br H Br H — CH₂(Ph-3,4-F₂)(Z) H G²-2Cl H CF₃ H — CH₂(Ph-3,5-F₂) H G²-2 Cl H Cl H — CH₂(Ph-3-F-4-Cl) H G²-2Cl H CF₃ H — CH₂(Ph-3,4-Cl₂) H G²-2 Cl H Cl H — CH₂(Ph-3-F-4-CF₃) H G²-2Cl H Cl H — CH₂(Ph-3-F-4-NO₂) H G²-2 Cl H Cl H — CH₂(Ph-3-F-4-CN) H G²-2Cl H Cl H — CH₂(Ph-2,3,4-F₃) H G²-2 Cl H Cl H — CH₂(Ph-2,4,5-F₃) H G²-2Cl H Cl H — CH₂(Ph-3,4,5-F₃) H G²-2 Cl H Cl H — CH₂(Ph-3,4,5-F₃)(Z) HG²-2 Cl H CF₃ H — CH₂(Ph-3,4,5-F₃) H G²-2 Cl H CF₃ H —CH₂(Ph-3,4,5-F₃)(Z) H G²-2 Cl H Cl H — CH₂(2-Naph) H G²-2 Cl H Cl H —CH₂(2-Naph)(Z) H G²-2 Cl H CF₃ H — CH₂(2-Naph) H G²-2 Cl H CF₃ H —CH₂(2-Naph)(Z) H G²-2 Cl H CF₃ H — CH₂(D-1-1b)-4-F H G²-2 Cl H Cl H —CH₂(D-1-1b)-4-Br H G²-2 Cl H CF₃ H — CH₂(D-1-1b)-5-F H G²-2 Cl H CF₃ H —CH₂(D-1-1b)-5-Cl H G²-2 Cl H Cl H — CH₂(D-1-1b)-5-Br CH₃ G²-2 Cl H Cl HH CH₂(D-1-1b)-5-CF₃ H G²-2 Cl H Cl H — CH₂(D-1-1b)-5-CF₃ H G²-2 Cl H CF₃H — CH₂(D-1-2b)-5-Cl H G²-2 Cl H Cl H — CH₂(D-1-2b)-5-Br H G²-2 Cl H CF₃H — CH₂(D-2-1b)-4-F H G²-2 Cl H Cl H — CH₂(D-2-1b)-4-Cl H G²-2 Cl H CF₃H — CH₂(D-2-1b)-5-F H G²-2 Cl H Cl H — CH₂(D-2-1b)-5-Cl H G²-2 Cl H CF₃H — CH₂(D-2-2b)-5-F H G²-2 Cl H Cl H — CH₂(D-2-2b)-5-Cl H G²-2 Cl H Cl H— CH₂(D-4-1b)-5-Cl H G²-2 Cl H CF₃ H — CH₂(D-5-3b)-3-Cl H G²-2 Cl H Cl H— CH₂(D-5-3b)-3-Br H G²-2 Cl H CF₃ H — CH₂(D-5-3b)-3-CH₃ H G²-2 Cl H ClH — CH₂(D-6-1b)-5-Br H G²-2 Cl H CF₃ H — CH₂(D-8-1b)-5-Cl H G²-2 Cl HCF₃ H — CH₂(D-8-3b)-3-Cl H G²-2 Cl H CF₃ H — CH₂(D-9-2b)-2-Cl H G²-2 ClH Cl H — CH₂(D-10-1a) H G²-2 Cl H Cl H — CH₂(D-10-1b)-4-Br H G²-2 Cl HCF₃ H — CH₂(D-10-1b)-5-F H G²-2 Cl H CF₃ H — CH₂(D-10-1b)-5-Cl H G²-2 ClH Cl H — CH₂(D-10-1b)-5-Br H G²-2 Cl H Cl H — CH₂(D-10-2a) H G²-2 Cl HCF₃ H — CH₂(D-10-2b)-2-F H G²-2 Cl H Cl H — CH₂(D-10-2b)-2-Cl H G²-2 ClH Cl H — CH₂(D-10-2b)-2-Br H G²-2 Cl H Cl H — CH₂(D-10-3b)-2-Cl H G²-2Cl H Cl H — CH₂(D-10-3b)-2-Br H G²-2 Cl H Cl H — CH₂(D-12-1b)-4-Cl HG²-2 Cl H CF₃ H — CH₂(D-12-1b)-5-Cl H G²-2 Cl H CF₃ H —CH₂(D-12-2b)-2-Cl H G²-2 Cl H Cl H — CH₂(D-14-1b)Br H G²-2 Cl H CF₃ H —CH₂(D-14-2b)Cl H G²-2 Cl H Cl H — CH₂(D-14-2b)Br H G²-2 Cl H CF₃ H —CH₂(D-15-1b)Cl H G²-2 Cl H CF₃ H — CH₂(D-17-b)Cl H G²-2 Cl H Cl H —CH₂(D-17-b)Br H G²-2 Cl H CF₃ H — CH₂(D-32-1a) H G²-2 Cl H CF₃ H —CH₂(D-32-1b)-5-F H G²-2 Cl H Cl H — CH₂(D-32-1b)-5-Cl H G²-2 Cl H Cl H —CH₂(D-32-1b)-5-Br H G²-2 Cl H CF₃ H — CH₂(D-32-2a) CH₃ G²-1 H H CF₃ H HCH₂(D-32-2b)-6-Cl CH₃ G²-1 H H OPh H H CH₂(D-32-2b)-6-Cl CH₃ G²-1 H H PhH H CH₂(D-32-2b)-6-Cl CH₃ G²-1 H F F F H CH₂(D-32-2b)-6-Cl CH₃ G²-1 H—CH═CHCH═CH— H H CH₂(D-32-2b)-6-Cl CH₃ G²-1 Cl H Cl H HCH₂(D-32-2b)-6-Cl CH₃ G²-1 Cl H Br H H CH₂(D-32-2b)-6-Cl H G²-2 Cl H ClH — CH₂(D-32-2b)-6-Cl H G²-2 Cl H CF₃ H — CH₂(D-32-2b)-6-Cl H G²-2 Cl HCF₃ H — CH₂(D-32-3a) CH₃ G²-1 Cl H Cl H H CH₂(D-32-3b)-2-Cl H G²-2 Cl HCl H — CH₂(D-32-3b)-2-Cl H G²-2 Cl H Cl H — CH₂(D-32-3b)-2-Cl(Z) H G²-2Cl H CF₃ H — CH₂(D-32-3b)-2-Cl H G²-2 Cl H CF₃ H — CH₂(D-32-3b)-2-Cl(Z)H G²-2 Cl H Cl H — CH₂(D-32-3b)-2,6-Cl₂ H G²-2 Cl H CF₃ H —CH₂(D-33-1b)-6-Cl H G²-2 Cl H Cl H — CH₂(D-33-1b)-6-Br H G²-2 Cl H CF₃ H— CH₂(D-34-1b)-5-Cl H G²-2 Cl H Cl H — CH₂(D-34-1b)-5-Br H G²-2 Cl H CF₃H — CH₂(D-34-2b)-2-Cl H G²-2 Cl H CF₃ H — CH₂(D-34-2b)-6-Cl H G²-2 Cl HCF₃ H — CH₂(D-34-3b)-6-Cl H G²-2 Cl H CF₃ H — CH₂(D-35-b)-5-F H G²-2 ClH CF₃ H — CH₂(D-35-b)-5-Cl H G²-2 Cl H Cl H — CH₂(D-35-b)-5-Br CH₃ G²-1H Cl Cl H H CH(CH₃)Ph CH₃ G²-1 Cl H H Cl H CH(CH₃)Ph H G²-2 F H Cl H —CH(CH₃)Ph H G²-2 F H Cl H — CH(CH₃)Ph(Z) H G²-2 Cl H F H — CH(CH₃)Ph HG²-2 Cl H F H — CH(CH₃)Ph(Z) H G²-2 Cl H Cl H — CH(CH₃)Ph H G²-2 Cl H ClH — CH(CH₃)Ph(Z) CH₃ G²-2 Cl H Cl H — CH(CH₃)Ph(Z) CH₃ G²-2 Cl H Cl H —CH(CH₃)Ph CH₃(S) G²-2 Cl H Cl H — CH(CH₃)Ph CH₃(S) G²-2 Cl H Cl H —CH(CH₃)Ph(Z) H G²-2 Cl H Cl F — CH(CH₃)Ph H G²-2 Cl H Cl F —CH(CH₃)Ph(Z) CH₃ G²-2 Cl H Cl F — CH(CH₃)Ph(Z) CH₃(S) G²-2 Cl H Cl F —CH(CH₃)Ph(Z) H G²-2 Cl H Br H — CH(CH₃)Ph H G²-2 Cl H Br H —CH(CH₃)Ph(Z) CH₃ G²-2 Cl H Br H — CH(CH₃)Ph(Z) CH₃(S) G²-2 Cl H Br H —CH(CH₃)Ph(Z) H G²-2 Cl H CF₃ H — CH(CH₃)Ph H G²-2 Cl H CF₃ H —CH(CH₃)Ph(Z) CH₃ G²-2 Cl H CF₃ H — CH(CH₃)Ph(Z) CH₃(S) G²-2 Cl H CF₃ H —CH(CH₃)Ph(Z) H G²-2 Cl H CN H — CH(CH₃)Ph H G²-2 Cl H C≡CH H — CH(CH₃)PhH G²-2 Cl H C≡CH H — CH(CH₃)Ph(Z) H G²-2 Cl H C≡CPr-c H — CH(CH₃)Ph HG²-2 Cl H C≡CPr-c H — CH(CH₃)Ph(Z) H G²-2 Cl H C≡CBu-t H — CH(CH₃)Ph HG²-2 Cl H C≡CBu-t H — CH(CH₃)Ph(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH(CH₃)Ph H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH(CH₃)Ph(Z) H G²-2 Cl HC≡CSi(CH₃)₃ H — CH(CH₃)Ph H G²-2 Cl H C≡CSi(CH₃)₃ H — CH(CH₃)Ph(Z) HG²-2 Cl H C≡CPh H — CH(CH₃)Ph H G²-2 Cl H C≡CPh H — CH(CH₃)Ph(Z) H G²-2Cl F Cl H — CH(CH₃)Ph H G²-2 Cl F Cl H — CH(CH₃)Ph(Z) H G²-2 Cl Cl Cl H— CH(CH₃)Ph H G²-2 Cl Cl Cl H — CH(CH₃)Ph(Z) H G²-2 Br H Cl H —CH(CH₃)Ph H G²-2 Br H Cl H — CH(CH₃)Ph(Z) H G²-2 Br H Br H — CH(CH₃)Ph HG²-2 Br H Br H — CH(CH₃)Ph(Z) CH₃ G²-2 Br H Br H — CH(CH₃)Ph(Z) CH₃(S)G²-2 Br H Br H — CH(CH₃)Ph(Z) CH₃ G²-10 Cl — H H — CH(CH₃)Ph H G²-2 Cl HCl H — CH(CH₃)(Ph-2-F) H G²-2 Cl H Cl H — CH(CH₃)(Ph-2-F)(Z) H G²-2 Cl HCF₃ H — CH(CH₃)(Ph-2-F) H G²-2 Cl H CF₃ H — CH(CH₃)(Ph-2-F)(Z) H G²-2 ClH Cl H — CH(CH₃)(Ph-3-F) H G²-2 Cl H Cl H — CH(CH₃)(Ph-3-F)(Z) CH₃ G²-2Cl H Cl H — CH(CH₃)(Ph-3-F)(Z) CH₃(S) G²-2 Cl H Cl H —CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl H Cl F — CH(CH₃)(Ph-3-F) H G²-2 Cl H Cl F —CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl H Cl Cl — CH(CH₃)(Ph-3-F) H G²-2 Cl H Br H— CH(CH₃)(Ph-3-F) H G²-2 Cl H Br H — CH(CH₃)(Ph-3-F)(Z) CH₃ G²-2 Cl H BrH — CH(CH₃)(Ph-3-F)(Z) CH₃(S) G²-2 Cl H Br H — CH(CH₃(Ph-3-F)(Z) H G²-2Cl H CF₃ H — CH(CH₃)(Ph-3-F) H G²-2 Cl H CF₃ H — CH(CH₃(Ph-3-F)(Z) CH₃G²-2 Cl H CF₃ H — CH(CH₃)(Ph-3-F)(Z) CH₃(S) G²-2 Cl H CF₃ H —CH(CH₃(Ph-3-F)(Z) H G²-2 Cl H C≡Pr-c H — CH(CH₃)(Ph-3-F) H G²-2 Cl HC≡CPr-c H — CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl H C≡CBu-t H — CH(CH₃(Ph-3-F) HG²-2 Cl H C≡CBu-t H — CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH(CH₃)(Ph-3-F) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH(CH₃)(Ph-3-F)(Z) H G²-2Cl H C≡CSi(CH₃)₃ H — CH(CH₃)(Ph-3-F) H G²-2 Cl H C≡CSi(CH₃)₃ H —CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl H C≡CPh H — CH(CH₃(Ph-3-F) H G²-2 Cl HC≡CPh H — CH(CH₃)(Ph-3-F)(Z) H G²-2 Cl F Cl H — CH(CH₃)(Ph-3-F) H G²-2Cl F Cl H — CH(CH₃)(Ph-3-F)(Z) H G²-2 Br H Cl H — CH(CH₃(Ph-3-F) H G²-2Br H Cl H — CH(CH₃)(Ph-3-F)(Z) H G²-2 Br H Br H — CH(CH₃)(Ph-3-F) H G²-2Br H Br H — CH(CH₃)(Ph-3-F)(Z) H G²-2 F H Cl H — CH(CH₃)(Ph-4-F) H G²-2P H Cl H — CH(CH₃)(Ph-4-F)(Z) Fl G²-2 Cl H F H — CH(CH₃)(Ph-4-F) H G²-2Cl H F H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H Cl H — CH(CH₃(Ph-4-F) H G²-2Cl H Cl H — CH(CH₃)(Ph-4-F)(F) H G²-2 Cl H Cl H — CH(CH₃)(Ph-4-F)(Z) H₃G²-2 Cl H Cl H — CH(CH₃)(Ph-4-F)(Z) CH₃(S) G²-2 Cl H Cl H —CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H Cl F — CH(CH₃(Ph-4-F) H G²-2 Cl H Cl F —CH(CH₃)(Ph-4-F)(Z) CH₃ G²-2 Cl H Cl F — CH(CH₃)(Ph-4-F)(Z) CH₃(S) G²-2Cl H Cl F — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H Br H — CH(CH₃)(Ph-4-F) H G²-2Cl H Br H — OH(CH₃)(Ph-4-F)(Z) CH₃ G²-2 Cl H Br H — CH(CH₃)(Ph-4-F)(Z)CH₃(S) G²-2 Cl H Br H — CH(CH₃(Ph-4-F)(Z) H G²-2 Cl H CF₃ H —CH(CH₃(Ph-4-F) H G²-2 Cl H CF₃ H — CH(CH₃)(Ph-4-F)(Z) CH₃ G²-2 Cl H CF₃H — CH(CH₃)(Ph-4 F)(Z) CH₃(S) G²-2 Cl H CF₃ H — CH(CH₃)(Ph-4-F)(Z) HG²-2 Cl H C≡CH H — CH(CH₃)(Ph-4-F) H G²-2 Cl H C≡CH H —CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H C≡CPr-c H — CH(CH₃)(Ph-4-F) H G²-2 Cl HC≡CPr-c H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H C≡CBu-t H — CH(CH₃)(Ph-4-F) HG²-2 Cl H C≡CBu-t H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H —CH(CH₃)(Ph-4-F) H G²-2 Cl H C≡CC(CH₃)₂OCH₃ H — CH(CH₃)(Ph-4-F)(Z) H G²-2Cl H C≡CSi(CH₃)₃ H — CH(CH₃)(Ph-4-F) H G²-2 Cl H C≡CSi(CH₃)₃ H —CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl H C≡CPh H — CH(CH₃)(Ph-4-F) H G²-2 Cl HC≡CPh H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl F Cl H — CH(CH₃)(Ph-4-F) H G²-2Cl F Cl H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Cl Cl Cl H — CH(CH₃)(Ph-4-F) HG²-2 Cl Cl Cl H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Br H Cl H — CH(CH₃)(Ph-4-F)H G²-2 Br H Cl H — CH(CH₃)(Ph-4-F)(Z) H G²-2 Br H Br H — CH(CH₃)(Ph-4-F)H G²-2 Br H Br H — CH(CH₃)(Ph-4-F)(Z) CH₃ G²-2 Br H Br H —CH(CH₃)(Ph-4-F)(Z) CH₃(S) G²-2 Br H Br H — CH(CH₃)(Ph-4-F)(Z) H G²-2 ClH Cl H — CH(CH₃)(D-1-1b)-4-Br H G²-2 Cl H CF₃ H — CH(CH₃)(D-1-1b)-5-Br HG²-2 Cl H Cl H — CH(CH₃)(D-2-1b)-4-Br H G²-2 Cl H Cl H —CH(CH₃)(D-2-1b)-5-Cl H G²-2 Cl H Cl H — CH(CH₃)(D-2-1b)-5-Br H G²-2 Cl HCF₃ H — CH(CH₃)(D-5-3b)-3-Cl H G²-2 Cl H Cl H — CH(CH₃)(D-5-3b)-3-Br HG²-2 Cl H Cl H — CH(CH₃)(D-10-1b)-4-Br H G²-2 Cl H Cl H —CH((CH₃)(D-10-1b)-5-Br H G²-2 Cl H CF₃ H — CH(CH₃)(D-10-2b)-2-Cl H G²-2Cl H Cl H — CH(CH₃)(D-10-2b)-2-Br H G²-2 Cl H CF₃ H —CH(CH₃)(D-10-3b)-2-Cl H G²-2 Cl H Cl H — CH(CH₃)(D-10-3b)-2-Br H G²-2 ClH CF₃ H — CH(CH₃)(D-32-1b)-5-F H G²-2 Cl H Cl H — CH(CH₃)(D-32-1b)-5-ClH G²-2 Cl H Cl H — CH(CH₃)(D-32-1b)-5-Br H G²-2 Cl H CF₃ H —CH(CH₃)(D-32-2b)-6-F H G²-2 Cl H Cl H — CH(CH₃)(D-32-2b)-6-Cl H G²-2 ClH Cl H — CH(CH₃)(D-32-2b)-6-Br H G²-2 Cl H CF₃ H — CH(CH₃)(D-32-3b)-2-FH G²-2 Cl H Cl H — CH(CH₃)(D-32-3b)-2-Cl H G²-2 Cl H Cl H —CH(CH₃)(D-32-3b)-2-Br H G²-2 Cl H CF₃ H — CH(CH₃)(D-34-1b)-5-F H G²-2 ClH Cl H — CH(CH₃)(D-34-2b)-2-Cl H G²-2 Cl H Cl H — CH(CH₃)(D-34-2b)-6-ClH G²-2 Cl H Cl H — CH(CH₃)(D-35-b)-5-Cl H G²-2 Cl H Cl H — C(CH₃)₂Ph HG²-2 Cl H Cl H — CH₂CH₂Ph H G²-2 Cl H CF₃ H — CH₂CH₂Ph H G²-2 Cl H Cl H— Ph

Compounds of Second Group ([I]-69 to [I]-92)

Combinations of substituents in the compounds of a second group areshown in Table 3.

TABLE 3 R⁴ R² R³ Y¹ Y² Y³ Y⁴ R¹ CH₃ H H Cl H Cl H CH₃ Et H H Cl H Cl HCH₃ i-Pr H H Cl H Cl H CH₃ c-Pr H H Cl H Cl H CH₃ c-Bu H H Cl H Cl H CH₃CH₂CHF₂ H H Cl H Cl H CH₃ CH₂OCH₃ H H Cl H Cl H CH₃ CH₂OEt H H Cl H Cl HCH₃ CH₂OC(O)CH₃ H H Cl H Cl H CH₃ CH₂OC(O)OCH₃ H H Cl H Cl H CH₃ CH₂SCH₃H H Cl H Cl H CH₃ CH₂CN H H Cl H Cl H CH₃ CH₂C(O)OCH₃ H H Cl H Cl H CH₃CH₂C(O)NH₂ H H Cl H Cl H CH₃ CH₂C(S)NH₂ H H Cl H Cl H CH₃ CH₂CH═CH₂ H HCl H Cl H CH₃ CH₂C≡CH H H Cl H Cl H CH₃ C(O)CH₃ H H Cl H Cl H CH₃ C(O)EtH H Cl H Cl H CH₃ C(O)Pr-n H H Cl H Cl H CH₃ C(O)Pr-i H H Cl H Cl H CH₃C(O)Pr-c H H Cl H Cl H CH₃ C(O)Bu-t H H Cl H Cl H CH₃ C(O)CH₂OCH₃ H H ClH Cl H CH₃ C(O)CH═CH₂ H H Cl H Cl H CH₃ C(O)OCH₃ H H Cl H Cl H CH₃C(O)OEt H H Cl H Cl H CH₃ C(O)OPr-i H H Cl H Cl H CH₃ C(O)OCH₂CH₂OCH₃ HH Cl H Cl H CH₃ C(O)OCH₂CH═CH₂ H H Cl H Cl H CH₃ OCH₃ H H Cl H Cl H CH₃OEt H H Cl H Cl H CH₃ SCCl₃ H H Cl H Cl H CH₃ Et H H Cl H Br H CH₃CH₂OCH₃ H H Cl H Br H CH₃ CH₂CN H H Cl H Br H CH₃ CH₂CH═CH₂ H H Cl H BrH CH₃ CH₂C≡CH H H Cl H Br H CH₃ C(O)CH₃ H H Cl H Br H CH₃ C(O)OCH₃ H HCl H Br H CH₃ CH₃ H H Cl H CF₃ H CH₃ Et H H Cl H CF₃ H CH₃ i-Pr H H Cl HCF₃ H CH₃ c-Pr H H Cl H CF₃ H CH₃ c-Bu H H Cl H CF₃ H CH₃ CH₂CHF₂ H H ClH CF₃ H CH₃ CH₂OCH₃ H H Cl H CF₃ H CH₃ CH₂OEt H H Cl H CF₃ H CH₃CH₂OC(O)CH₃ H H Cl H CF₃ H CH₃ CH₂OC(O)OCH₃ H H Cl H CF₃ H CH₃ CH₂SCH₃ HH Cl H CF₃ H CH₃ CH₂CN H H Cl H CF₃ H CH₃ CH₂C(O)OCH₃ H H Cl H CF₃ H CH₃CH₂C(O)NH₂ H H Cl H CF₃ H CH₃ CH₂C(S)NH₂ H H Cl H CF₃ H CH₃ CH₂CH═CH₂ HH Cl H CF₃ H CH₃ CH₂C≡CH H H Cl H CF₃ H CH₃ C(O)CH₃ H H Cl H CF₃ H CH₃C(O)Et H H Cl H CF₃ H CH₃ C(O)Pr-n H H Cl H CF₃ H CH₃ C(O)Pr-i H H Cl HCF₃ H CH₃ C(O)Pr-c H H Cl H CF₃ H CH₃ C(O)Bu-t H H Cl H CF₃ H CH₃C(O)CH₂OCH₃ H H Cl H CF₃ H CH₃ C(O)CH═CH₂ H H Cl H CF₃ H CH₃ C(O)OCH₃ HH Cl H CF₃ H CH₃ C(O)OEt H H Cl H CF₃ H CH₃ C(O)OPr-i H H Cl H CF₃ H CH₃C(O)OCH₂CH₂OCH₃ H H Cl H CF₃ H CH₃ C(O)OCH₂CH═CH₂ H H Cl H CF₃ H CH₃OCH₃ H H Cl H CF₃ H CH₃ OEt H H Cl H CF₃ H CH₃ SCCl₃ H H Cl H CF₃ H CH₃Et H H Cl H C≡CBu-t H CH₃ CH₂OCH₃ H H Cl H C≡CBu-t H CH₃ CH₂CN H H Cl HC≡CBu-t H CH₃ CH₂CH═CH₂ H H Cl H C≡CBu-t H CH₃ CH₂C≡CH H H Cl H C≡CBu-tH CH₃ C(O)CH₃ H H Cl H C≡CBu-t H CH₃ C(O)OCH₃ H H Cl H C≡CBu-t H CH₃ EtH H Cl H C≡CSi(CH₃)₃ H CH₃ CH₂OCH₃ H H Cl H C≡CSi(CH₃)₃ H CH₃ CH₂CN H HCl H C≡CSi(CH₃)₃ H CH₃ CH₂CH═CH₂ H H Cl H C≡CSi(CH₃)₃ H CH₃ CH₂C≡CH H HCl H C≡CSi(CH₃)₃ H CH₃ C(O)CH₃ H H Cl H C≡CSi(CH₃)₃ H CH₃ C(O)OCH₃ H HCl H C≡CSi(CH₃)₃ H CH₃ Et H H Cl H C≡CPh H CH₃ CH₂OCH₃ H H Cl H C≡CPh HCH₃ CH₂CN H H Cl H C≡CPh H CH₃ CH₂CH═CH₂ H H Cl H C≡CPh H CH₃ CH₂C≡CH HH Cl H C≡CPh H CH₃ C(O)CH₃ H H Cl H C≡CPh H CH₃ C(O)OCH₃ H H Cl H C≡CPhH CH₃ Et H H Br H Br H CH₃ CH₂OCH₃ H H Br H Br H CH₃ CH₂CN H H Br H Br HCH₃ CH₂CH═CH₂ H H Br H Br H CH₃ CH₂C≡CH H H Br H Br H CH₃ C(O)CH₃ H H BrH Br H CH₃ C(O)OCH₃ H H Br H Br H CH₃ Et CH₃ H Cl H Cl H CH₃ CH₂OCH₃ CH₃H Cl H Cl H CH₃ CH₂CN CH₃ H Cl H Cl H CH₃ CH₂CH═CH₂ CH₃ H Cl H Cl H CH₃CH₂C≡CH CH₃ H Cl H Cl H CH₃ C(O)CH₃ CH₃ H Cl H Cl H CH₃ C(O)OCH₃ CH₃ HCl H Cl H CH₃ Et CH₃ H Cl H CF₃ H CH₃ CH₂OCH₃ CH₃ H Cl H CF₃ H CH₃ CH₂CNCH₃ H Cl H CF₃ H CH₃ CH₂CH═CH₂ CH₃ H Cl H CF₃ H CH₃ CH₂C≡CH CH₃ H Cl HCF₃ H CH₃ C(O)CH₃ CH₃ H Cl H CF₃ H CH₃ C(O)OCH₃ CH₃ H Cl H CF₃ H CH₃ HCH₃ CH₃ Cl H Cl H CH₃ H CH₃ CH₃ Cl H Cl H CH₃(Z) H CH₃ CH₃ Cl H Br H CH₃H CH₃ CH₃ Cl H Br H CH₃(Z) H CH₃ CH₃ Cl H CF₃ H CH₃ H CH₃ CH₃ Cl H CF₃ HCH₃(Z) H CH₃ CH₃ Cl H C≡CBu-t H CH₃ H CH₃ CH₃ Cl H C≡CBu-t H CH₃(Z) HCH₃ CH₃ Cl H C≡CSi(CH₃)₃ H CH₃ H CH₃ CH₃ Cl H C≡CSi(CH₃)₃ H CH₃(Z) H CH₃CH₃ Cl H C≡CPh H CH₃ H CH₃ CH₃ Cl H C≡CPh H CH₃(Z) H CH₃ CH₃ Br H Br HCH₃ H CH₃ CH₃ Br H Br H CH₃(Z) H —CH₂CH₂— Cl H Cl H CH₃ H —CH₂CH₂— Cl HCl H CH₃(Z) H —CH₂CH₂— Cl H Cl F CH₃ H —CH₂CH₂— Cl H Cl F CH₃(Z) H—CH₂CH₂— Cl H Br H CH₃ H —CH₂CH₂— Cl H Br H CH₃(Z) H —CH₂CH₂— Cl H CF₃ HCH₃ H —CH₂CH₂— Cl H CF₃ H CH₃(Z) H —CH₂CH₂— Cl H C≡CBu-t H CH₃ H—CH₂CH₂— Cl H C≡CBu-t H CH₃(Z) H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₃ H—CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₃(Z) H —CH₂CH₂— Cl H C≡CPh H CH₃ H—CH₂CH₂— Cl H C≡CPh H CH₃(Z) H —CH₂CH₂— Br H Br H CH₃ H —CH₂CH₂— Br H BrH CH₃(Z) H —CH₂CH₂CH₂— Cl H Cl H CH₃ H —CH₂CH₂CH₂— Cl H Cl H CH₃(Z) H—CH₂CH₂CH₂— Cl H Br H CH₃ H —CH₂CH₂CH₂— Cl H Br H CH₃(Z) H —CH₂CH₂CH₂—Cl H CF₃ H CH₃ H —CH₂CH₂CH₂— Cl H CF₃ H CH₃(Z) H —CH₂CH₂CH₂— Cl HC≡CBu-t H CH₃ H —CH₂CH₂CH₂— Cl H C≡CBu-t H CH₃(Z) H —CH₂CH₂CH₂— Cl HC≡CSi(CH₃)₃ H CH₃ H —CH₂CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₃(Z) H —CH₂CH₂CH₂—Cl H C≡CPh H CH₃ H —CH₂CH₂CH₂— Cl H C≡CPh H CH₃(Z) H —CH₂CH₂CH₂— Br H BrH CH₃ H —CH₂CH₂CH₂— Br H Br H CH₃(Z) H —CH₂OCH₂— Cl H Cl H CH₃ H—CH₂OCH₂— Cl H Cl H CH₃(Z) H —CH₂OCH₂— Cl H Br H CH₃ H —CH₂OCH₂— Cl H BrH CH₃(Z) H —CH₂OCH₂— Cl H CF₃ H CH₃ H —CH₂OCH₂— Cl H CF₃ H CH₃(Z) H—CH₂OCH₂— Cl H C≡CBu-t H CH₃ H —CH₂OCH₂— Cl H C≡CBu-t H CH₃(Z) H—CH₂OCH₂— Cl H C≡CSi(CH₃)₃ H CH₃ H —CH₂OCH₂— Cl H C≡CSi(CH₃)₃ H CH₃(Z) H—CH₂OCH₂— Cl H C≡CPh H CH₃ H —CH₂OCH₂— Cl H C≡CPh H CH₃(Z) H —CH₂OCH₂—Br H Br H CH₃ H —CH₂OCH₂— Br H Br H CH₃(Z) H —CH₂OCH₂— Cl H Cl H CH₃ H—CH₂SCH₂— Cl H Cl H CH₃(Z) H —CH₂SCH₂— Cl H CF₃ H CH₃ H —CH₂SCH₂— Cl HCF₃ H CH₃(Z) H —CH₂CH₂CH₂CH₂— Cl H Cl H CH₃ H —CH₂CH₂CH₂CH₂— Cl H CF₃ HCH₃ H —CH₂OCH₂CH₂— Cl H Cl H CH₃ H —CH₂OCH₂CH₂— Cl H Cl H CH₃(Z) H—CH₂OCH₂CH₂— Cl H Br H CH₃ H —CH₂OCH₂CH₂— Cl H CF₃ H CH₃ H —CH₂OCH₂CH₂—Cl H CF₃ H CH₃(Z) H —CH₂OCH₂CH₂— Cl H C≡CBu-t H CH₃ H —CH₂OCH₂CH₂— Cl HC≡CSi(CH₃)₃ H CH₃ H —CH₂OCH₂CH₂— Cl H C≡CPh H CH₃ H —CH₂OCH₂CH₂— Br H BrH CH₃ H —CH₂SCH₂CH₂— Cl H Cl H CH₃ H —CH₂SCH₂CH₂— Cl H CF₃ H CH₃ H—CH₂S(O)CH₂CH₂— Cl H Cl H CH₃ H —CH₂S(O)CH₂CH₂— Cl H CF₃ H CH₃ H—CH₂SO₂CH₂CH₂— Cl H Cl H CH₃ H —CH₂SO₂CH₂CH₂— Cl H CF₃ H CH₃ Et H H Cl HCl H Et CH₂OCH₃ H H Cl H Cl H Et CH₂CN H H Cl H Cl H Et CH₂CH═CH₂ H H ClH Cl H Et CH₂C≡CH H H Cl H Cl H Et C(O)CH₃ H H Cl H Cl H Et C(O)OCH₃ H HCl H Cl H Et Et H H Cl H CF₃ H Et CH₂OCH₃ H H Cl H CF₃ H Et CH₂CN H H ClH CF₃ H Et CH₂CH═CH₂ H H Cl H CF₃ H Et CH₂C≡CH H H Cl H CF₃ H Et C(O)CH₃H H Cl H CF₃ H Et C(O)OCH₃ H H Cl H CF₃ H Et H CH₃ CH₃ Cl H Cl H Et HCH₃ CH₃ Cl H Cl H Et(Z) H CH₃ CH₃ Cl H CF₃ H Et H CH₃ CH₃ Cl H CF₃ HEt(Z) H —CH₂CH₂— Cl H Cl H Et H —CH₂CH₂— Cl H Cl H Et(Z) H —CH₂CH₂— Cl HCl F Et H —CH₂CH₂— Cl H Cl F Et(Z) H —CH₂CH₂— Cl H Br H Et H —CH₂CH₂— ClH Br H Et(Z) H —CH₂CH₂— Cl H CF₃ H Et H —CH₂CH₂— Cl H CF₃ H Et(Z) H—CH₂CH₂— Cl H C≡CBu-t H Et H —CH₂CH₂— Cl H C≡CBu-t H Et(Z) H —CH₂CH₂— ClH C≡CSi(CH₃)₃ H Et H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H Et(Z) H —CH₂CH₂— Cl HC≡CPh H Et H —CH₂CH₂— Cl H C≡CPh H Et(Z) H —CH₂CH₂— Br H Br H Et H—CH₂CH₂— Br H Br H Et(Z) H —CH₂CH₂CH₂— Cl H Cl H Et H —CH₂CH₂CH₂— Cl HCl H Et(Z) H —CH₂CH₂CH₂— Cl H CF₃ H Et H —CH₂CH₂CH₂— Cl H CF₃ H Et(Z) H—CH₂OCH₂— Cl H Cl H Et H —CH₂OCH₂— Cl H Cl H Et(Z) H —CH₂OCH₂— Cl H Br HEt H —CH₂OCH₂— Cl H Br H Et(Z) H —CH₂OCH₂— Cl H CF₃ H Et H —CH₂OCH₂— ClH CF₃ H Et(Z) H —CH₂OCH₂— Cl H C≡CBu-t H Et H —CH₂OCH₂— Cl H C≡CBu-t HEt(Z) H —CH₂OCH₂— Cl H C≡CSi(CH₃)₃ H Et H —CH₂OCH₂— Cl H C≡CSi(CH₃)₃ HEt(Z) H —CH₂OCH₂— Cl H C≡CPh H Et H —CH₂OCH₂— Cl H C≡CPh H Et(Z) H—CH₂OCH₂— Br H Br H Et H —CH₂OCH₂— Br H Br H Et(Z) H —CH₂SCH₂— Cl H Cl HEt H —CH₂SCH₂— Cl H CF₃ H Et H —CH₂OCH₂CH₂— Cl H Cl H Et H —CH₂OCH₂CH₂—Cl H CF₃ H Et H CH₃ CH₃ Cl H Cl H n-Pr H CH₃ CH₃ Cl H CF₃ H n-Pr H—CH₂CH₂— Cl H Cl H n-Pr H —CH₂CH₂— Cl H Cl H n-Pr(Z) H —CH₂CH₂— Cl H BrH n-Pr H —CH₂CH₂— Cl H CF₃ H n-Pr H —CH₂CH₂— Cl H CF₃ H n-Pr(Z) H—CH₂CH₂— Cl H C≡CBu-t H n-Pr H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H n-Pr H—CH₂CH₂— Cl H C≡CPh H n-Pr H —CH₂CH₂— Br H Br H n-Pr H —CH₂CH₂CH₂— Cl HCl H n-Pr H —CH₂CH₂CH₂— Cl H CF₃ H n-Pr H —CH₂OCH₂— Cl H Cl H n-Pr H—CH₂OCH₂— Cl H Cl H n-Pr(Z) H —CH₂OCH₂— Cl H CF₃ H n-Pr H —CH₂OCH₂— Cl HCF₃ H n-Pr(Z) Et H H Cl H Cl H i-Pr CH₂OCH₃ H H Cl H Cl H i-Pr CH₂CN H HCl H Cl H i-Pr CH₂CH═CH₂ H H Cl H Cl H i-Pr CH₂C≡CH H H Cl H Cl H i-PrC(O)CH₃ H H Cl H Cl H i-Pr C(O)OCH₃ H H Cl H Cl H i-Pr Et H H Cl H CF₃ Hi-Pr CH₂OCH₃ H H Cl H CF₃ H i-Pr CH₂CN H H Cl H CF₃ H i-Pr CH₂CH═CH₂ H HCl H CF₃ H i-Pr CH₂C≡CH H H Cl H CF₃ H i-Pr C(O)CH₃ H H Cl H CF₃ H i-PrC(O)OCH₃ H H Cl H CF₃ H i-Pr H CH₃ CH₃ Cl H Cl H i-Pr H CH₃ CH₃ Cl H ClH i-Pr(Z) H CH₃ CH₃ Cl H CF₃ H i-Pr H CH₃ CH₃ Cl H CF₃ H i-Pr(Z) H—CH₂CH₂— Cl H Cl H i-Pr H —CH₂CH₂— Cl H Cl H i-Pr(Z) H —CH₂CH₂— Cl H ClF i-Pr H —CH₂CH₂— Cl H Cl F i-Pr(Z) H —CH₂CH₂— Cl H Br H i-Pr H —CH₂CH₂—Cl H Br H i-Pr(Z) H —CH₂CH₂— Cl H CF₃ H i-Pr H —CH₂CH₂— Cl H CF₃ Hi-Pr(Z) H —CH₂CH₂— Cl H C≡CBu-t H i-Pr H —CH₂CH₂— Cl H C≡CBu-t H i-Pr(Z)H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H i-Pr H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H i-Pr(Z)H —CH₂CH₂— Cl H C≡CPh H i-Pr H —CH₂CH₂— Cl H C≡CPh H i-Pr(Z) H —CH₂CH₂—Br H Br H i-Pr H —CH₂CH₂— Br H Br H i-Pr(Z) H —CH₂CH₂CH₂— Cl H Cl H i-PrH —CH₂CH₂CH₂— Cl H Cl H i-Pr(Z) H —CH₂CH₂CH₂— Cl H CF₃ H i-Pr H—CH₂CH₂CH₂— Cl H CF₃ H i-Pr(Z) H —CH₂OCH₂— Cl H Cl H i-Pr H —CH₂OCH₂— ClH Cl H i-Pr(Z) H —CH₂OCH₂— Cl H Br H i-Pr H —CH₂OCH₂— Cl H Br H i-Pr(Z)H —CH₂OCH₂— Cl H CF₃ H i-Pr H —CH₂OCH₂— Cl H CF₃ H i-Pr(Z) H —CH₂OCH₂—Cl H C≡CBu-t H i-Pr H —CH₂OCH₂— Cl H C≡CBu-t H i-Pr(Z) H —CH₂OCH₂— Cl HC≡CSi(CH₃)₃ H i-Pr H —CH₂OCH₂— Cl H C≡CSi(CH₃)₃ H i-Pr(Z) H —CH₂OCH₂— ClH C≡CPh H i-Pr H —CH₂OCH₂— Cl H C≡CPh H i-Pr(Z) H —CH₂OCH₂— Br H Br Hi-Pr H —CH₂OCH₂— Br H Br H i-Pr(Z) H —CH₂SCH₂— Cl H Cl H i-Pr H—CH₂SCH₂— Cl H CF₃ H i-Pr H —CH₂OCH₂CH₂— Cl H Cl H i-Pr H —CH₂OCH₂CH₂—Cl H CF₃ H i-Pr H —CH₂CH₂— Cl H Cl H n-Bu H —CH₂CH₂— Cl H Cl H n-Bu(Z) H—CH₂CH₂— Cl H CF₃ H n-Bu H —CH₂CH₂— Cl H CF₃ H n-Bu(Z) H —CH₂OCH₂— Cl HCl H n-Bu H —CH₂OCH₂— Cl H CF₃ H n-Bu H —CH₂CH₂— Cl H Cl H i-Bu H—CH₂CH₂— Cl H Cl H i-Bu(Z) H —CH₂CH₂— Cl H CF₃ H i-Bu H —CH₂CH₂— Cl HCF₃ H i-Bu(Z) H —CH₂OCH₂— Cl H Cl H i-Bu H —CH₂OCH₂— Cl H CF₃ H i-Bu HCH₃ CH₃ Cl H Cl H CH₂Pr-c H CH₃ CH₃ Cl H CF₃ H CH₂Pr-c H —CH₂CH₂— Cl HCl H CH₂Pr-c H —CH₂CH₂— Cl H Cl H CH₂Pr-c(Z) H —CH₂CH₂— Cl H Br HCH₂Pr-c H —CH₂CH₂— Cl H CF₃ H CH₂Pr-c H —CH₂CH₂— Cl H CF₃ H CH₂Pr-c(Z) H—CH₂CH₂— Cl H C≡CBu-t H CH₂Pr-c H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₂Pr-c H—CH₂CH₂— Cl H C≡CPh H CH₂Pr-c H —CH₂CH₂— Br H Br H CH₂Pr-c H —CH₂CH₂CH₂—Cl H Cl H CH₂Pr-c H —CH₂CH₂CH₂— Cl H CF₃ H CH₂Pr-c H —CH₂OCH₂— Cl H Cl HCH₂Pr-c H —CH₂OCH₂— Cl H Cl H CH₂Pr-c(Z) H —CH₂OCH₂— Cl H CF₃ H CH₂Pr-cH —CH₂OCH₂— Cl H CF₃ H CH₂Pr-c(Z) H CH₃ CH₃ Cl H Cl H s-Bu H CH₃ CH₃ ClH CF₃ H s-Bu H —CH₂CH₂— Cl H Cl H s-Bu H —CH₂CH₂— Cl H Cl H s-Bu(Z) H—CH₂CH₂— Cl H Br H s-Bu H —CH₂CH₂— Cl H CF₃ H s-Bu H —CH₂CH₂— Cl H CF₃ Hs-Bu(Z) H —CH₂CH₂— Cl H C≡CBu-t H s-Bu H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ Hs-Bu H —CH₂CH₂— Cl H C≡CPh H s-Bu H —CH₂CH₂— Br H Br H s-Bu H—CH₂CH₂CH₂— Cl H Cl H s-Bu H —CH₂CH₂CH₂— Cl H CF₃ H s-Bu H —CH₂OCH₂— ClH Cl H s-Bu H —CH₂OCH₂— Cl H Cl H s-Bu(Z) H —CH₂OCH₂— Cl H CF₃ H s-Bu H—CH₂OCH₂— Cl H CF₃ H s-Bu(Z) H CH₃ CH₃ Cl H Cl H t-Bu H CH₃ CH₃ Cl H CF₃H t-Bu H —CH₂CH₂— Cl H Cl H t-Bu H —CH₂CH₂— Cl H Cl H t-Bu(Z) H —CH₂CH₂—Cl H Br H t-Bu H —CH₂CH₂— Cl H CF₃ H t-Bu H —CH₂CH₂— Cl H CF₃ H t-Bu(Z)H —CH₂CH₂— Cl H C≡CBu-t H t-Bu H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H t-Bu H—CH₂CH₂— Cl H C≡CPh H t-Bu H —CH₂CH₂— Br H Br H t-Bu H —CH₂CH₂CH₂— Cl HCl H t-Bu H —CH₂CH₂CH₂— Cl H CF₃ H t-Bu H —CH₂OCH₂— Cl H Cl H t-Bu H—CH₂OCH₂— Cl H Cl H t-Bu(Z) H —CH₂OCH₂— Cl H CF₃ H t-Bu H —CH₂OCH₂— Cl HCF₃ H t-Bu(Z) H —CH₂CH₂— Cl H Cl H CH(Et)₂ H —CH₂CH₂— Cl H Cl HCH(Et)₂(Z) H —CH₂CH₂— Cl H CF₃ H CH(Et)₂ H —CH₂CH₂— Cl H CF₃ HCH(Et)₂(Z) H —CH₂OCH₂— Cl H Cl H CH(Et)₂ H —CH₂OCH₂— Cl H CF₃ H CH(Et)₂H —CH₂CH₂— Cl H Cl H c-Pen H —CH₂CH₂— Cl H Cl H c-Pen(Z) H —CH₂CH₂— Cl HCF₃ H c-Pen H —CH₂CH₂— Cl H CF₃ H c-Pen(Z) H —CH₂OCH₂— Cl H Cl H c-Pen H—CH₂OCH₂— Cl H CF₃ H c-Pen H CH₃ CH₃ Cl H Cl H CH₂CHF₂ H CH₃ CH₃ Cl HCF₃ H CH₂CHF₂ H —CH₂CH₂— Cl H Cl H CH₂CHF₂ H —CH₂CH₂— Cl H Cl HCH₂CHF₂(Z) H —CH₂CH₂— Cl H Br H CH₂CHF₂ H —CH₂CH₂— Cl H CF₃ H CH₂CHF₂ H—CH₂CH₂— Cl H CF₃ H CH₂CHF₂(Z) H —CH₂CH₂— Cl H C≡CBu-t H CH₂CHF₂ H—CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₂CHF₂ H —CH₂CH₂— Cl H C≡CPh H CH₂CHF₂ H—CH₂CH₂— Br H Br H CH₂CHF₂ H —CH₂CH₂CH₂— Cl H Cl H CH₂CHF₂ H —CH₂CH₂CH₂—Cl H CF₃ H CH₂CHF₂ H —CH₂OCH₂— Cl H Cl H CH₂CHF₂ H —CH₂OCH₂— Cl H Cl HCH₂CHF₂(Z) H —CH₂OCH₂— Cl H CF₃ H CH₂CHF₂ H —CH₂OCH₂— Cl H CF₃ HCH₂CHF₂(Z) H CH₃ CH₃ Cl H Cl H CH₂CF₃ H CH₃ CH₃ Cl H CF₃ H CH₂CF₃ H—CH₂CH₂— Cl H Cl H CH₂CF₃ H —CH₂CH₂— Cl H Cl H CH₂CF₃(Z) H —CH₂CH₂— Cl HBr H CH₂CF₃ H —CH₂CH₂— Cl H CF₃ H CH₂CF₃ H —CH₂CH₂— Cl H CF₃ H CH₂CF₃(Z)H —CH₂CH₂— Cl H C≡CBu-t H CH₂CF₃ H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₂CF₃ H—CH₂CH₂— Cl H C≡CPh H CH₂CF₃ H —CH₂CH₂— Br H Br H CH₂CF₃ H —CH₂CH₂CH₂—Cl H Cl H CH₂CF₃ H —CH₂CH₂CH₂— Cl H CF₃ H CH₂CF₃ H —CH₂OCH₂— Cl H Cl HCH₂CF₃ H —CH₂OCH₂— Cl H Cl H CH₂CF₃(Z) H —CH₂OCH₂— Cl H CF₃ H CH₂CF₃ H—CH₂OCH₂— Cl H CF₃ H CH₂CF₃(Z) H CH₃ CH₃ Cl H Cl H CH₂CH═CH₂ H CH₃ CH₃Cl H CF₃ H CH₂CH═CH₂ H —CH₂CH₂— Cl H Cl H CH₂CH═CH₂ H —CH₂CH₂— Cl H Cl HCH₂CH═CH₂(Z) H —CH₂CH₂— Cl H Br H CH₂CH═CH₂ H —CH₂CH₂— Cl H CF₃ HCH₂CH═CH₂ H —CH₂CH₂— Cl H CF₃ H CH₂CH═CH₂(Z) H —CH₂CH₂— Cl H C≡CBu-t HCH₂CH═CH₂ H —CH₂CH₂— Cl H C≡CSi(CH₃)₃ H CH₂CH═CH₂ H —CH₂CH₂— Cl H C≡CPhH CH₂CH═CH₂ H —CH₂CH₂— Br H Br H CH₂CH═CH₂ H —CH₂CH₂CH₂— Cl H Cl HCH₂CH═CH₂ H —CH₂CH₂CH₂— Cl H CF₃ H CH₂CH═CH₂ H —CH₂OCH₂— Cl H Cl HCH₂CH═CH₂ H —CH₂OCH₂— Cl H Cl H CH₂CH═CH₂(Z) H —CH₂OCH₂— Cl H CF₃ HCH₂CH═CH₂ H —CH₂OCH₂— Cl H CF₃ H CH₂CH═CH₂(Z) H CH₃ CH₃ Cl H Cl HCH(CH₃)CH═CH₂ H CH₃ CH₃ Cl H CF₃ H CH(CH₃)CH═CH₂ H —CH₂CH₂— Cl H Cl HCH(CH₃)CH═CH₂ H —CH₂CH₂— Cl H Cl H CH(CH₃)CH═CH₂(Z) H —CH₂CH₂— Cl H Br HCH(CH₃)CH═CH₂ H —CH₂CH₂— Cl H CF₃ H CH(CH₃)CH═CH₂ H —CH₂CH₂— Cl H CF₃ HCH(CH₃)CH═CH₂(Z) H —CH₂CH₂— Cl H C≡CBu-t H CH(CH₃)CH═CH₂ H —CH₂CH₂— Cl HC≡CSi(CH₃)₃ H CH(CH₃)CH═CH₂ H —CH₂CH₂— Cl H C≡CPh H CH(CH₃)CH═CH₂ H—CH₂CH₂— Br H Br H CH(CH₃)CH═CH₂ H —CH₂CH₂CH₂— Cl H Cl H CH(CH₃)CH═CH₂ H—CH₂CH₂CH₂— Cl H CF₃ H CH(CH₃)CH═CH₂ H —CH₂OCH₂— Cl H Cl H CH(CH₃)CH═CH₂H —CH₂OCH₂— Cl H Cl H CH(CH₃)CH═CH₂(Z) H —CH₂OCH₂— Cl H CF₃ HCH(CH₃)CH═CH₂ H —CH₂OCH₂— Cl H CF₃ H CH(CH₃)CH═CH₂(Z) H —CH₂CH₂— Cl H ClH CH₂(Ph-4-F) H —CH₂CH₂— Cl H Cl H CH₂(Ph-4-F)(Z) H —CH₂CH₂— Cl H CF₃ HCH₂(Ph-4-F) H —CH₂CH₂— Cl H CF₃ H CH₂(Ph-4-F)(Z) H —CH₂OCH₂— Cl H Cl HCH₂(Ph-4-F) H —CH₂OCH₂— Cl H CF₃ H CH₂(Ph-4-F) H —CH₂CH₂— Cl H Cl HCH₂(Ph-4-Cl) H —CH₂CH₂— Cl H Cl H CH₂(Ph-4-Cl)(Z) H —CH₂CH₂— Cl H CF₃ HCH₂(Ph-4-Cl) H —CH₂CH₂— Cl H CF₃ H CH₂(Ph-4-Cl)(Z) H —CH₂OCH₂— Cl H Cl HCH₂(Ph-4-Cl) H —CH₂OCH₂— Cl H CF₃ H CH₂(Ph-4-Cl) H —CH₂CH₂— Cl H Cl HCH₂(Ph-4-CN) H —CH₂CH₂— Cl H Cl H CH₂(Ph-4-CN)(Z) H —CH₂CH₂— Cl H CF₃ HCH₂(Ph-4-CN) H —CH₂CH₂— Cl H CF₃ H CH₂(Ph-4-CN)(Z) H —CH₂OCH₂— Cl H Cl HCH₂(Ph-4-CN) H —CH₂OCH₂— Cl H CF₃ H CH₂(Ph-4-CN) H —CH₂CH₂— Cl H Cl HCH₂(Ph-3,4-F₂) H —CH₂CH₂— Cl H Cl H CH₂(Ph-3,4-F₂)(Z) H —CH₂CH₂— Cl HCF₃ H CH₂(Ph-3,4-F₂) H —CH₂CH₂— Cl H CF₃ H CH₂(Ph-3,4-F₂)(Z) H —CH₂OCH₂—Cl H Cl H CH₂(Ph-3,4-F₂) H —CH₂OCH₂— Cl H CF₃ H CH₂(Ph-3,4-F₂) H—CH₂CH₂— Cl H Cl H CH(CH₃)Ph H —CH₂CH₂— Cl H Cl H CH(CH₃)Ph(Z) H—CH₂CH₂— Cl H CF₃ H CH(CH₃)Ph H —CH₂CH₂— Cl H CF₃ H CH(CH₃)Ph(Z) H—CH₂OCH₂— Cl H Cl H CH(CH₃)Ph H —CH₂OCH₂— Cl H CF₃ H CH(CH₃)Ph H—CH₂CH₂— Cl H Cl H CH(CH₃)(Ph-4-F) H —CH₂CH₂— Cl H Cl HCH(CH₃)(Ph-4-F)(Z) H —CH₂CH₂— Cl H CF₃ H CH(CH₃)(Ph-4-F) H —CH₂CH₂— Cl HCF₃ H CH(CH₃)(Ph-4-F)(Z) H —CH₂OCH₂— Cl H Cl H CH(CH₃)(Ph-4-F) H—CH₂OCH₂— Cl H CF₃ H CH(CH₃)(Ph-4-F)

The compounds of the present invention are capable of controllingpathogens causing plant diseases in Tracheophyta such as plants of theorder Pinales, the group magnoliids, the group monocots and the groupeudicots, and pathogens causing infections of Vertebrata such as animalsof the class Mammalia, the class Ayes, the class Reptilia and the classActinopterygii, and pests such as plant-parasitic or animal-parasiticnematodes, Acanthocephala, Platyhelminthes and Protozoa.

Pests against plants may, for example, be fungi of the phylumAscomycota, fungi of the phylum Basidiomycota, fungi of the phylumChitridiomycota, fungi of the phylum Blastocladiomycota, fungi of thephylum Mucoromycotina, protists of the phylum Cercozoa, microorganismsof the phylum Heterokontophyta class Oomycetes, gram-positive bacteriaof the phylum Actinobacteria, gram-positive bacteria of the phylumTenericutes, gram-negative bacteria of the phylum Proteobacteria,nematodes of the order Aphelenchida and nematodes of the orderTylenchida. The compounds of the present invention have excellentcontrolling effect particularly on plant pathogenic fungi belonging tothe phylum Ascomycota and the phylum Basidiomycota, and plant-parasiticnematodes belonging to the order Aphelenchida and the order Tylenchidaat low doses.

Pests against animals may, for example, be fungi of the phylumAscomycota, fungi of the phylum Basidiomycota, gram-positive bacteria ofthe phylum Actinobacteria, gram-positive bacteria of the phylumFirmicutes, gram-positive bacteria of the phylum Tenericutes,gram-negative bacteria of the phylum Proteobacteria, nematodes of theorder Enoplida, nematodes of the order Rhabditida, nematodes of theorder Strongylida, nematodes of the order Ascaridida, nematodes of theorder Spirurida, microorganisms of the phylum Acanthocephala, cestodesof the order Pseudophyllidea, cestodes of the order Cyclophyllidea,trematodes of the order Strigeidida, trematodes of the orderEchinostomida, trematodes of the order Plagiorchiida, trematodes of theorder Opisthorchiida, amebas, Piroplasmida sporozoa, Haemosporidasporozoa, Eucoccidiorida sporozoa, Vestibuliferida ciliata,Trichomonadida flagellata, Diplomonadida flagellata and Kinetoplastidaflagellata. Particularly, the compounds of the present invention haveexcellent effect to control internal parasites parasitizing animals ofthe class Mammalia belonging to the family Cebidae, the familyCercopithecidae, the family Homimidae, the family Leporidae, the familyChinchillidae, the family Caviidae, the family Cricetidae, the familyMuridae, the family Sciuridae, the family Camelidae, the family Suidae,the family Cervidae, the family Bovidae, the family Felidae, the familyCanidae, the family Mustelidae, the family Equidae, the familyMacropodidae and the like, especially animal-parasitic nematodesbelonging to the order Enoplida, the order Rhabditida, the orderStrongylida, the order Aphelenchida, the order Tylenchida, the orderAscaridida and the order Spirurida, parasitizing mammals of the familySuidae, the family Bovidae, the family Felidae, the family Canidae andthe family Equidae.

The compounds of the present invention are also effective on pests whichhave acquired resistance to conventional fungicides or nematicides, andthe compounds of the present invention have very useful characteristicssuch that they have little harmful effect on non-target animals such asmammals, fishes, crustaceans, natural enemies and useful insects.

The compounds of the present invention may be used in any dosage formsuch as a soluble concentrate, an emulsifiable concentrate, a wettablepowder, a water soluble powder, a water dispersible granule, a watersoluble granule, a suspension concentrate, a concentrated emulsion, asuspoemulsion, a microemulsion, a dustable powder, a granule, a tabletor an emulsifiable gel usually after mixed with an appropriate solidcarrier or a liquid carrier, and if necessary, with a surfactant, apenetrant, a spreader, a thickener, an anti-freezing agent, a binder, ananti-caking agent, a disintegrant, an antifoaming agent, a preservative,a stabilizer or the like. A formulation in an arbitrary dosage form maybe sealed in water-soluble packaging such as a water-soluble capsule ora water-soluble film, for labor saving or improved safety.

As solid carriers, natural minerals such as quartz, calcite, meerschaum,dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite,methahalloysite, kibushi clay, gairome clay, pottery stone, zeeklite,allophone, Shirasu, mica, talc, bentonite, activated clay, acid clay,pumice, attapulgite, zeolite and diatomaceous earth, calcined naturalminerals such as calcined clay, pearlite, Shirasu-balloons, vermiculite,attapulgus clay and calcined diatomaceous earth, inorganic salts such asmagnesium carbonate, calcium carbonate, sodium carbonate, sodiumhydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate,diammonium hydrogen phosphate, ammonium dihydrogen phosphate andpotassium chloride, saccharides such as glucose, fructose, sucrose andlactose, polysaccharides such as starch, cellulose powder and dextrin,organic substances such as urea, urea derivatives, benzoic acid andbenzoic acid salts, plants such as wood flour, powdered cork, corncob,walnut shell and tobacco stems, fly ash, white carbon (such as hydratedsynthetic silica, anhydrous synthetic silica and hydrous syntheticsilicate), fertilizers and the like may be mentioned.

As liquid carriers, aromatic hydrocarbons such as xylene, alkyl (C₉ orC₁₀ etc.) benzene, phenylxylylethane and alkyl (C₁ or C₃etc.)naphthalene, aliphatic hydrocarbons such as machine oil, normalparaffin, isoparaffin and naphthene, mixtures of aromatic hydrocarbonsand aliphatic hydrocarbons such as kerosene, alcohols such as ethanol,isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, polyhydricalcohols such as ethylene glycol, propylene glycol, diethylene glycol,hexylene glycol, polyethylene glycol and polypropylene glycol, etherssuch as propyl cellosolve, butyl cellosolve, phenyl cellosolve,propylene glycol monomethyl ether, propylene glycol monoethyl ether,propylene glycol monopropyl ether, propylene glycol monobutyl ether andpropylene glycol monophenyl ether, ketones such as acetophenone,cyclohexanone and γ-butyrolactone, esters such as fatty acid methylesters, dialkyl succinates, dialkyl glutamate, dialkyl adipates anddialkyl phthalates, acid amides such as N— alkyl (C₁, C₈ or C₁₂etc.)pyrrolidone, fats and oils such as soybean oil, linseed oil,rapeseed oil, coconut oil, cottonseed oil and castor oil, dimethylsulfoxide, water and the like may be mentioned.

These solid and liquid carriers may be used alone or in combinations oftwo or more.

As surfactants, nonionic surfactants such as polyoxyethylene alkylether, polyoxyethylene alkyl(mono or di)phenyl ether,polyoxyethylene(mono, di or tri)styrylphenyl ether,polyoxyethylenepolyoxypropylene block copolymers, polyoxyethylene fattyacid (mono or di)ester, sorbitan fatty acid ester, polyoxyethylenesorbitan fatty acid ester, ethylene oxide adducts of castor oil,acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetyleneglycol, ethylene oxide adducts of acetylene alcohol and alkylglycosides, anionic surfactants such as alkyl sulfate salts,alkylbenzenesulfonic acid salts, lignin sulfonate, alkylsulfosuccinicacid salts, naphthalenesulfonic acid salts, alkylnaphthalenesulfonicacid salts, salts of naphthalenesulfonic acid-formalin condensates,salts of alkylnaphthalenesulfonic acid-formalin condensates,polyoxyethylene alkyl ether sulfate or phosphate salts,polyoxyethylene(mono or di) alkylphenyl ether sulfate or phosphatesalts, polyoxyethylene(mono, di or tri)styrylphenyl ether sulfate orphosphate salts, polycarboxylic acid salts (such as polyacrylates,polymaleates and copolymers of maleic acid and an olefin) andpolystyrenesulfonic acid salts, cationic surfactants such as alkylaminesalts and alkyl quaternary ammonium salts, amphoteric surfactants suchas amino acid types and betaine types, silicone surfactants and fluorinesurfactants may be mentioned.

The amount of these surfactants is usually preferred to be from 0.05 to20 parts by weight per 100 parts by weight of the agent of the presentinvention, though there is no particular restrictions. These surfactantsmay be used alone or in combination of two or more.

The suitable application dose of the compounds of the present inventionis generally about from 0.005 to 50 kg per hectare (ha) in terms of theactive ingredient, though it varies depending on the applicationsituation, the application season, the application method and thecultivated crop.

When the compounds of the present invention are used to control internalparasites in mammals and birds as farm animals/poultry and pet animals,the compounds of the present invention may be administered in aneffective amount together with pharmaceutically acceptable additivesorally, parenterally by injection (intramuscular, subcutaneously,intravenously or intraperitoneally); percutaneously by dipping,spraying, bathing, washing, pouring-on and spotting-on and dusting, orintranasally. The compounds of the present invention may be administeredthrough molded articles such as chips, plates, bands, collars, earmarks, limb bands and ID tags. The compounds of the present inventionare administered in an arbitrary dosage form suitable for theadministration route.

The dosage form may be a solid preparation such as a dust, a granule, awettable powder, a pellet, a tablet, a ball, a capsule and an moldedarticle containing an active ingredient, a liquid preparation such as aninjection fluid, an oral liquid, a liquid preparation applied to theskin or coelom, a pour-on preparation, a spot-on preparation, aflowable, an emulsion, and a semisolid preparation such as an ointmentand a gel.

A solid preparation may generally be used by oral administration or bypercutaneous or by environmental application after dilution with wateror the like. A solid preparation can be prepared by mixing an activeingredient with an appropriate vehicle, and with an adjuvant ifnecessary, and formulating the mixture into a desired dosage form. Asthe vehicle, an inorganic vehicle such as a carbonate, a hydrogencarbonate, a phosphate, aluminum oxide, silica or clay or an organicvehicle such as a saccharide, cellulose, cereal flour or starch may, forexample, be mentioned.

An injection fluid may be administered intravenously, intramuscularly orsubcutaneously. An injection fluid can be prepared by dissolving anactive ingredient in an appropriate solvent and, if necessary, addingadditives such as a solubilizer, an acid, a base, a buffering salt, anantioxidant and a protectant. As appropriate solvents, water, ethanol,butanol, benzyl alcohol, glycerin, propylene glycol, polyethyleneglycol, N-methylpyrrolidone and mixtures thereof, physiologicallyacceptable vegetable oils and synthetic oils suitable for injection maybe mentioned. As solubilizers, polyvinylpyrrolidone, polyoxyethylatedcastor oil, polyoxyethylated sorbitan ester and the like may bementioned. As protectants, benzyl alcohol, trichlorobutanol,p-hydroxybenzoic acid esters, n-butanol and the like may be mentioned.

An oral liquid may be administered directly or after dilution and can beprepared in the same manner as an injection fluid.

A flowable, an emulsion or the like may be administered directly orafter dilution percutaneously or by environmental application.

A liquid preparation applied to the skin is administered by dripping,spreading, rubbing, spraying, sprinkling or dipping (soaking, bathing orwashing) and can be prepared in the same manner as an injection fluid.

A pour-on preparation and a spot-on preparation are dripped or sprayedto a limited area of the skin so that they permeate through the skin andact systemically. A pour-on preparation and a spot-on preparation can beprepared by dissolving, suspending or emulsifying an active ingredientin an appropriate skin-friendly solvent or solvent mixture. Ifnecessary, additives such as a surfactant, a colorant, anabsorbefacient, an antioxidant, a light stabilizer and an adhesive maybe added.

As appropriate solvents, water, alkanol, glycol, polyethylene glycol,polypropylene glycol, glycerin, benzyl alcohol, phenylethanol,phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate,dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether,acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons,vegetable or synthetic oils, DMF, liquid paraffin, light liquidparaffin, silicone, dimethylacetamide, N-methylpyrrolidone or2,2-dimethyl-4-oxy-methylene-1,3-dioxolane may be mentioned. Asabsorbefacients, DMSO, isopropyl myristate, pelargonic acid dipropyleneglycol, silicone oil, fatty acid esters, triglycerides and aliphaticalcohols may be mentioned. As antioxidants, sulfites, metabisulfites,ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherolmay be mentioned.

An emulsion may be administered orally, percutaneously or by injection.An emulsion can be prepared by dissolving an active ingredient in ahydrophobic phase or a hydrophilic phase and homogenizing the resultingsolution with another liquid phase together with an appropriateemulsifier, and further if necessary with additives such as a colorant,an absorbefacient, a protectant, an antioxidant, a light screen and athickner.

As hydrophobic phases (oils), paraffin oil, silicone oil, sesame oil,almond oil, castor oil, synthetic triglycerides, ethyl stearate,di-n-butyryl adipate, hexyl laurate, pelargonic acid dipropylene glycol,esters of branched short-chain fatty acids with C₁₆-C₁₈ saturated fattyacids, isopropyl myristate, isopropyl palmitate, esters of C₁₂-C₁₈saturated alcohols with caprylic/capric acid, isopropyl stearate, oleyloleate, decyl oleate, ethyl oleate, ethyl lactate, fatty acid esterwaxes, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol,2-octyldodecanol, cetylstearyl alcohol and oleyl alcohol may bementioned.

As hydrophilic phases, water, propylene glycol, glycerin and sorbitolmay be mentioned.

As emulsifiers, nonionic surfactants such as polyoxyethylated castoroil, polyoxyethylated sorbitan monoolefinic acid, sorbitan monostearate,glycerin monostearate, polyoxyethyl stearate and alkyl phenol polyglycolether; amphoteric surfactants such as disodiumN-lauryl-β-iminodipropionate and lecithin; anionic surfactants such assodium lauryl sulfate, aliphatic alcohol sulfate ether,mono/dialkylpolyglycol orthophosphate monoethanolamine salt; andcationic surfactants such as cetyltrimethylammonium chloride may, forexample, be mentioned.

As other additives, carboxymethylcellulose, methylcellulose,polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone,polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymers,polyethylene glycol, waxes and colloidal silica may be mentioned.

A semisolid preparation is administered by applying or spreading ontothe skin or introducing into the coelom. A gel can be prepared by addinga thickener to a solution prepared in the same manner as an injectionfluid sufficiently to give a transparent viscous substance like anointment.

Formulation examples of preparations using the compounds of the presentinvention are given below. However, formulations of the presentinvention are by no means restricted thereto. In the followingformulation examples, “parts” means parts by weight.

[Wettable Powder]

Compound of the present invention 0.1 to 80 parts Solid carrier 5 to98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts

As the others, an anti-caking agent, a stabilizer and the like may bementioned.

[Emulsifiable Concentrate]

Compound of the present invention 0.1 to 30 parts Organic solvent 45 to95 parts Surfactant 4.9 to 30 parts Water 0 to 50 parts Others 0 to 10parts

As the others, a spreader, a stabilizer and the like may be mentioned.

[Suspension Concentrate]

Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts

As the others, an anti-freezing agent, a thickener and the like may bementioned.

[Water Dispersible Granule]

Compound of the present invention 0.1 to 90 parts Solid carrier 0 to98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts

As the others, a binder, a stabilizer and the like may be mentioned.

[Soluble Concentrate]

Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to99.99 parts Others 0 to 10 parts

As the others, an anti-freezing agent, a spreader and the like may bementioned.

[Granule]

Compound of the present invention 0.01 to 80 parts Solid carrier 10 to99.99 parts Others 0 to 10 parts

As the others, a binder, a stabilizer and the like may be mentioned.

[Dustable Powder]

Compound of the present invention 0.01 to 30 parts Solid carrier 65 to99.99 parts Others 0 to 5 parts

As the others, an anti-drift agent, a stabilizer and the like may bementioned.

Next, more specific examples of preparations containing compounds of thepresent invention as an active ingredient are given below. However, thepresent invention is by no means restricted thereto.

In the following Formulation Examples, “parts” means parts by weight.

Formulation Example 1 Wettable Powder

Compound No. 2-132 of the present invention 20 parts Pyrophyllite 74parts Sorpol 5039 4 parts (tradename for a mixture of a nonionicsurfactant and an anionic surfactant: manufactured by TOHO ChemicalIndustry Col., Ltd.) CARPLEX #80D 2 parts (hydrous synthetic silicicacid: tradename manufactured by Shionogi & Co., Ltd.)

The above ingredients are mixed and pulverized homogenously to obtain awettable powder.

Formulation Example 2 Emulsifiable Concentrate

Compound No.2-124 of the present invention  5 parts Xylene 75 partsN-methylpyrrolidone 15 parts Sorpol 2680  5 parts (tradename for amixture of a nonionic surfactant and an anionic surfactant: manufacturedby TOHO Chemical Industry Co., Ltd.)

The above ingredients are mixed homogenously to obtain an emulsifiableconcentrate.

Formulation Example 3 Emulsifiable Concentrate

Compound No.2-117 of the present invention  4 parts DBE 36 parts(tradename for a mixture of dimethyl adipate, dimethyl glutarate anddimethyl succinate: manufactured by INVISTA) Diisobutyl adipate 30 partsN-methylpyrrolidone 10 parts Soprofol BSU 14 parts (tradename for anonionic surfactant: manufactured by Rhodia Nicca.Ltd.) Rhodacal 70BC  6parts (tradename for an anionic surfactant: manufactured by RhodiaNicca.Ltd.)

The above ingredients are mixed homogenously to obtain an emulsifiableconcentrate.

Formulation Example 4 Emulsifiable Concentrate

Compound No.2-020 of the present invention  4 parts DBE 11 parts(tradename for a mixture of dimethyl adipate, dimethyl glutarate anddimethyl succinate: manufactured by INVISTA) Diisobutyl adipate 30 partsN-methylpyrrolidone  5 parts Soprofol BSU 14 parts (tradename for anonionic surfactant: manufactured by Rhodia Nicca.Ltd.) Rhodacal 70BC  6parts (tradename for an anionic surfactant: manufactured by RhodiaNicca.Ltd.) Propylene glycol 10 parts Water 20 parts

The above ingredients are mixed homogenously to obtain an emulsifiableconcentrate.

Formulation Example 5 Suspension Concentrate

Compound No.2-136 of the present invention   25 parts AGRISOL S-710   10parts (tradename for a nonionic surfactant: manufactured by KaoCorporation) Lunox 1000C  0.5 part (tradename for an anionic surfactant:manufactured by TOHO Chemical Industry Co., Ltd.) Xanthan gum  0.2 partWater 64.3 parts

The above ingredients are mixed homogenously and wet-pulverized toobtain a suspension concentration.

Formulation Example 6 Water Soluble Granule

Compound No.2-128 of the present invention 75 parts HITENOL NE-15  5parts (tradename for an anionic surfactant: manufactured by Dai-ichiKogyo Seiyaku Co., Ltd.) VANILLEX N 10 parts (tradename for an anionicsurfactant: manufactured by Nippon Paper Industries Co., LTD.) CARPLEX#80D 10 parts (tradename for hydrous synthetic silicic acid:manufactured by Shionogi & Co., Ltd.)

The above ingredients are mixed and pulverized homogenously, thenkneaded with a small amount of water, granulated through an extrusiongranulator and dried to obtain a water soluble granule.

Formulation Example 7 Granule

Compound No.2-120 of the present invention  5 parts Bentonite 50 partsTalc 45 parts

The above ingredients are mixed and pulverized homogenously, thenkneaded with a small amount of water, granulated through an extrusiongranulator and dried to obtain a granule.

Formulation Example 8 Dustable Powder

Compound No.2-140 of the present invention   3 parts CARPLEX #80D 0.5part (tradename for a hydrous synthetic silicic acid: manufactured byShionogi & Co., Ltd.) Kaolinite  95 parts Diisopropyl phosphate 1.5parts

The above ingredients are mixed and pulverized homogeneously to obtain adustable powder.

It is applied after diluted with water by a factor of from 1 to 20000 soas to achieve an active ingredient concentration of from 0.005 to 50kg/ha.

Formulation Example 9 Wettable Powder Preparation

Compound No.2-126 of the present invention 25 parts Sodiumdiisobutylnaphthalenesulfonate  1 part Calcium n-dodecylbenzenesulfonate10 parts Alkyl aryl polyglycol ether 12 parts Naphthalenesulfonicacid-formalin condensate sodium salt  3 parts Silicone emulsion  1 partSilicon dioxide  3 parts Kaolin 45 parts

Formulation Example 10 Water-Soluble Concentrate Preparation

Compound No.2-212 of the present invention   20 partsPolyoxyethylenelauryl ether   3 parts Sodium dioctylsulfosuccinate  3.5parts Dimethyl sulfoxide   37 parts 2-Propanol 36.5 parts

Formulation Example 11 Liquid Preparation for Spraying

Compound No.2-185 of the present invention  2 parts Dimethyl sulfoxide10 parts 2-Propanol 35 parts Acetone 53 parts

Formulation Example 12 Liquid Preparation for PercutaneousAdministration

Compound No.2-151 of the present invention  5 parts Hexylene glycol 50parts Isopropanol 45 parts

Formulation Example 13 Liquid Preparation for PercutaneousAdministration

Compound No.2-114 of the present invention  5 parts Propylene glycolmonomethyl ether 50 parts Dipropylene glycol 45 parts

Formulation Example 14 Liquid Preparation for PercutaneousAdministration (by Dripping)

Compound No.2-174 of the present invention  2 parts Light liquidparaffin 98 parts

Formulation Example 15 Liquid Preparation for PercutaneousAdministration (by Dripping)

Compound No.2-240 of the present invention  2 parts Light liquidparaffin 58 parts Olive oil 30 parts ODO-H  9 parts Shin-etsu silicone 1 part

For use as agricultural fungicides or nematocides, if necessary, thecompounds of the present invention may be mixed with other fungicides,other nematocides, insecticides, miticides, plant growth regulators,herbicides, synergists, fertilizers, soil conditioners and the like atthe time of formulation or application.

Further, for use as internal parasiticides, the compounds of the presentinvention in effective amounts may be applied alone as activeingredients, or if necessary, they may be mixed with other antibiotics,other vermicides and the like at the time of formulation or application.

Particularly, the combined use with other fungicides, other nematocides,other antibiotics, other vermicides or the like is expected to broadenthe pesticidal spectrum by the additive or synergistic effect of theother agrochemicals, to improve the pesticidal effect, to reduce theapplication cost by enabling control at lower doses, and further, toprolong the pesticidal effect for a long period of time. Particularly,the combined use with other fungicides, nematocides, antibiotics orvermicides differing in the mechanism of action is a very usefulcontrolling method with a view to preventing the pests from acquiringresistance to pesticides. In such cases, they may be combined with aplurality of known fungicides, known nematocides, known insecticides,known miticides, known antibiotics or known vermicides simultaneously.

The fungicides, nematocides, insecticides, miticides, vermicides andantibiotics to be used in combination with the compounds of the presentinvention include, for example, the compounds disclosed in e.g. ThePesticidal Manual, 15th edition, 2009, having the generic names listedbelow, but are not necessarily restricted thereto.

Fungicides: such as acibenzolar-5-methyl, acypetacs, aldimorph,ametoctradin, amisulbrom, amobam, ampropylfos, anilazine, azaconazole,azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl,benthiavalicarb-isopropyl, benthiazole, benzovindiflupyr, biphenyl,bitertanol, bixafen, bordeaux mixture, boscalid, bromuconazole,bupirimate, calcium polysulfide, captan, carbendazim, carboxin,carpropamid, carvone, cheshunt mixture, chinomethionat, chloroneb,chloropicrin, chlorothalonil, chiozolinate, climbazole, coppercarbonate, basic, copper hydroxide, copper naphthenate, copper oleate,copper oxychloride, copper sulfate, copper sulfate, basic,coumoxystrobin, cresol, cufraneb, cyazofamid, cyflufenamid, cymoxanil,cyproconazole, cyprodinil, dazomet, dichlofluanid, dichlorophen,diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb,difenoconazole, diflumetorim, dimethomorph, dimoxystrobin, diniconazole,diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, diphenylamine,dithianon, DNOC, dodemorph-acetate, dodine, drazoxolon, edifenphos,enestrobin, enoxastrobin, epoxiconazole, etaconazole, ethaboxam,ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone,fenaminstrobin, fenarimol, fenbuconazole, fenfuram, fenhexamid,fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph,fenpyrazamine, fentin, ferbam, ferimzone, fluazinam, fludioxonil,flufenoxystrobin, flumorph, fluopicolide, fluopyram, fluoroimide,fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet,fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furconazole,furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazol,imazalil, imibenconazole, iminoctadine-albesilate,iminoctadine-triacetate, ipconazole, iprobenfos, iprodione,iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil,kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb,mandestrobin, mandipropamid, maneb, mepanipyrim, mepronil, metalaxyl,metalaxyl-M, metam, metconazole, methfuroxam, metiram, metominostrobin,metrafenone, metsulfovax, milneb, myclobutanil, nabam, natamycin, nickelbis(dimethyldithiocarbamate), nitrothal-isopropy, nuarimol, ofurace,orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazolefumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol (PCP), penthiopyrad, 2-phenylphenol, phthalide,picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim,potassium azide, potassium hydrogen carbonate, probenazole, prochloraz,procymidone, propamocarb hydrochloride, propiconazole, propineb,proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyrazophos, pyribencarb-methyl, pyrifenox, pyrimethanil,pyriminostrobin, pyriofenone, pyrisoxazole, pyroquilon,quinacetol-sulfate, quinoxyfen, quintozene, sedaxane, silthiofam,simeconazole, sodium hydrogen carbonate, sodium hypochlorite,spiroxamine, sulfur, tebuconazole, tebufloquin, tecoram, tetraconazole,thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil,tolciofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol,triazoxide, tributyltin oxide, triclopyricab, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole, validamycin,valifenalate, vinclozolin, zinc naphthenate, zinc sulfate, ziram,zoxamide, shiitake mushroom mycelium extracts, shiitake mushroomfruiting body extracts, BCF-082 (experimental name), NNF-0721(experimental name) and ZF-9646 (experimental name).

Insecticides: such as abamectin, acephate, acetamiprid, afidopyropen,afoxolaner, alanycarb, aldicarb, allethrin, azamethiphos,azinphos-ethyl, azinphos-methyl, bacillus thuringiensis, bendiocarb,benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin,bioresmethrin, bistrifluoron, buprofezin, butocarboxim, carbaryl,carbofuran, carbosulfan, cartap, chlorantraniliprole, chlorethoxyfos,chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos,chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin,cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin,cyphenothrin, cyromazine, deltamethrin, diafenthiuron, diazinon,dichlorvos, diflubenzuron, dimethoate, dimethylvinphos, dinotefuran,diofenolan, disulfoton, emamectin-benzoate, empenthrin, endosulfan,alpha-endosulfan, EPN, esfenvalerate, ethiofencarb, ethiprole,etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenthion,fenvalerate, fipronil, flometoquin, flonicamid, fluazuron,flubendiamide, flucycloxuron, flucythrinate, flufenerim, flufenoxuron,flufiprole, flumethrin, flupyradifurone, fluralaner, fluvalinate,tau-fluvalinate, fonofos, furathiocarb, halofenozide, heptafluthrin,hexaflumuron, hydramethylnon, imidacloprid, imiprothrin, indoxacarb,indoxacarb-MP, isoprocarb, isoxathion, lepimectin, lufenuron, malathion,meperfluthrin, metaflumizone, metaldehyde, methacrifos, methamidophos,methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide,metofluthrin, muscalure, nitenpyram, novaluron, noviflumuron, omethoate,oxydemeton-methyl, parathion-methyl, permethrin, phenothrin, phenthoate,phorate, phosalone, phosmet, phoxim, pirimicarb, pirimiphos-methyl,profenofos, prothiofos, pymetrozine, pyraclofos, pyrethrins, pyridalyl,pyrifluquinazon, pyriprole, pyriproxyfen, resmethrin, rotenone,silafluofen, spinetoram, spinosad, spirotetramat, sulfotep, sulfoxaflor,tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos,tetramethrin, d-T-80-phthalthrin (d-tetramethrin), tetramethylfluthrin,thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon,tolfenpyrad, tralomethrin, transfluthrin, triazamate, trichlorfon,triflumuron, ME5382 (experimental name), NC-515 (experimental name) andZDI2501 (experimental name).

Miticides: such as acequinocyl, acrinathrin, amidoflumet, amitraz,azocyclotin, benzoximate, bifenazate, bromopropylate, clofentezine,cyenopyrafen, cyflumetofen, dicofol, dienochlor, etoxazole, fenazaquin,fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate,fluacrypyrim, formetanate, halfenprox, hexythiazox, milbemectin,propargite, pyflubumide, pyridaben, pyrimidifen, spirodiclofen,spiromesifen, tebufenpyrad and NA-89 (experimental name).

Nematicides: such as cadusafos, dichlofenthion, ethoprophos, fenamiphos,fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos,methyl bromide, methyl isothiocyanate, oxamyl, sodium azide, BYI-1921(experimental name) and MAI-08015 (experimental name).

Vermicides: such as acriflavine, albendazole, atovaguone, azithromycin,bithionol, bromofenofos, cambendazole, camidazole, chloroquine,clazuril, clindamycin hydrochloride, clorsulon, closantel, coumaphos,cymiazol, dichlorophen, diethylcarbamazine, diminazene, disophenol,dithiazanine iodide, doxycycline hydrochloride, doramectin, emodepside,eprinomectin, febantel, fenbendazole, flubendazole, furazolidone,glycalpyramide, imidocarb, ivermectin, levamisole, mebendazole,mefloquine, melarsamine hydrochloride, metronidazole, metyridine,milbemycin oxime, monepantel, morantel tartrate, moxidectin, nicarbazin,niclosamide, nitroscanate, nitroxynil, omphalotin, oxantel pamoate,oxantel tartrate, oxfendazolee, oxibendazole, oxyclozanide, pamaquine,phenothiazine, piperazine adipate, piperazine citrate, piperazinephosphate, PNU-97333 (paraherquamide A), PNU-141962(2-deoxyparaherquamide), praziquantel, primaquine, propetamphos,propoxur, pyrantel pamoate, pyrimethamine, santonin, selamectin,sulfadimethoxine, sulfadoxine, sulfamerazine, sulfamonomethoxine,sulfamoildapsone, thiabendazole, tinidazole, toltrazuril, tribromsalanand triclabendazole.

Antifungal agents: such as ketoconazole and miconazole nitrate.

Antibiotics: such as amoxicillin, ampicillin, bethoxazin, bithionol,bronopol, cefapirin, cefazolin, cefquinome, ceftiofur,chlortetracycline, clavulanic acid, danofloxacin, difloxacin,dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin,marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin,octhilinone, ofloxacin, orbifloxacin, oxolinic acid, oxytetracycline,penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosinphosphate, acetylisovaleryltylosin, tylosin phosphate, tulathromycin,valnemulin, calcinated shell calcium (calcium oxide), Talaromyces,Trichoderma and Coniothyrium.

EXAMPLES

The present invention will be described in further detail by referringto the following specific Examples of synthesis of and tests on thecompounds of the present invention. However, the present invention is byno means restricted thereto.

Synthetic Examples Synthetic Example 1(Z)—N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 1-004 of the Present Invention) Step 1: Preparation of2-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime

To 4.00 g of 2-bromo-1-(2,4-dichlorophenyl)ethanone in 20 ml of ethanol,1.25 g of methoxyamine hydrochloride was added, and the mixture wasstirred at room temperature for 12 hours. After completion of thereaction, the solvent was evaporated under reduced pressure, and theresulting residue was mixed with 20 ml of water and extracted with ethylacetate (20 ml×2). The resulting organic layers were combined, washedwith water (20 ml×1) and then dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure to obtain 3.85 g of the desired crudeproduct as a pale yellow oil. The oil was used in the next step withoutfurther purification.

¹H NMR (CDCl₃, Me₄ Si, 300 MHz) δ7.2-7.55 (m, 3H), 4.56 and 4.35 (s,2H), 4.06 and 4.04 (s, 3H).

Step 2: Preparation ofN-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]phthalimide

To 2.17 g of 2-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime in 20ml of N,N-dimethylformamide, 3.03 g of potassium phthalimide and 1.61 gof potassium carbonate were added, and the mixture was stirred at roomtemperature for 18 hours. After completion of the reaction, the reactionmixture was mixed with 40 ml of water and extracted with ethyl acetate(50 ml×1), the resulting organic layer was washed with water (20 ml×1)and then dried over saturated aqueous sodium chloride and then anhydroussodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as theeluent to obtain 2.10 g of the desired product as pale yellow crystals.

m.p.: 82.0-85.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ7.65-7.8 (m, 4H), 7.15-7.35 (m, 3H),4.92 (s, 2H), 4.01 (s, 3H).

Step 3: Preparation of2-amino-1-(2,4-dichlorophenyl)ethanone-O-methyloxime

To 316 mg of N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]phthalimidein 10 ml of ethanol, 108 mg of hydrazine monohydrate was added, and themixture was stirred at 60° C. for 2 hours. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 30 ml of water and extracted with ethyl acetate (40 ml×1).The resulting organic layer was dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure to obtain 170 mg of the desired crudeproduct as a colorless oil. The oil was used in the next step withoutfurther purification.

¹H NMR (CDCl₃, Me_(a)Si, 300 MHz) δ7.25-7.45 (m, 3H), 3.99 (s, 3H), 3.82(s, 2H).

Step 4: Preparation of(Z)—N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a solution of 170 mg of2-amino-1-(2,4-dichlorophenyl)ethanone-β-methyloxime and 74 mg oftriethylamine in 5 ml of dichloromethane, 122 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise, and the mixturewas stirred at room temperature for 1 hour. After completion of thereaction, the reaction mixture was mixed with 10 ml of water andextracted with chloroform (20 ml×1), the resulting organic layer wasdried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was mixed with 3 ml of diisopropyl ether andcrystallized to obtain 110 mg of the desired product as white crystals.

m.p.: 146.0-148.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ7.25-7.7 (m, 6H), 7.05-7.15 (m, 1H),6.31 (bs, 1H), 4.62 (d, J=6.3 Hz, 2H), 4.02 (s, 3H).

Synthetic Example 2(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-120 of the Present Invention) Step 1: Preparation of1-(3,5-dichloropyridin-2-yl)ethanone

To 20 g of 3,5-dichloropyridine-2-carbonitrile in 150 ml oftetrahydrofuran, 139 ml of a 1M tetrahydrofuran solution ofmethylmagnesium bromide was added dropwise with stirring under coolingwith ice, and the mixture was stirred at the same temperature for 1hour. After completion of the reaction, the reaction mixture was mixedwith 15 ml of concentrated hydrochloric acid and 100 ml of water andextracted with ethyl acetate (100 ml×2), the resulting organic layerswere combined, washed with water (100 ml×1) and dried over saturatedaqueous solution chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue wasdissolved in 40 ml of ethyl acetate and 10 ml of hexane, 20 g of silicagel was added, the mixture was stirred at room temperature for 1 hourand then subjected to filtration, and the solvent was evaporated underreduced pressure. The precipitated solid was washed with 50 ml of hexaneto obtain 17.16 g of the desired product as pale yellow crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.82 (d, J=2.1Hz, 1H), 2.68 (s, 3H).

Step 2: Preparation of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone

To 5.00 g of 1-(3,5-dichloropyridin-2-yl)ethanone in 75 ml oftetrahydrofuran, 9.94 g of trimethylphenylammonium tribromide was added,and the mixture was stirred at room temperature for 16 hours. Aftercompletion of the reaction, the precipitated solid was filtered offthrough celite, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 5:95 to 15:85) asthe eluent to obtain 6.64 g of the desired product as a brown oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 (d, J=1.9 Hz, 1H), 7.88 (d, J=1.9Hz, 1H), 4.67 (s, 2H).

Step 3: Preparation of2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-ethyloxime

To 3.00 g of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone in 25 ml ofethanol, 1.09 g of ethoxyamine hydrochloride was added, and the mixturewas stirred at room temperature for 16 hours. After completion of thereaction, the solvent was evaporated under reduced pressure, theresulting residue was mixed with 50 ml of water and extracted with ethylacetate (50 ml×2), the resulting organic layers were combined, washedwith water (50 ml×1) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatograph using ethyl acetate-hexane (with a gradient of from5:95 to 15:85) as the eluent to obtain 3.03 g of the desired product asa colorless oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.81 (d, J=2.1Hz, 1H), 4.67 and 4.52 (s, 2H), 4.35 and 4.32 (q, J=7.2 Hz, 2H), 1.37and 1.36 (t, J=7.2 Hz, 3H).

Step 4: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]phthalimide

To 3.00 g of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-ethyloximein 20 ml of N,N-dimethylformamide, 2.32 g of potassium phthalimide wasadded, and the mixture was stirred at room temperature for 12 hours.After completion of the reaction, the reaction mixture was mixed with 50ml of water and extracted with ethyl acetate (100 ml×1), the resultingorganic layer was washed with water (50 ml×1) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waswashed with 10 ml of diisopropyl ether to obtain 3.08 g of the desiredproduct as white crystals. m.p.: 99.0 to 101.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.29 (d, J=2.1 Hz, 1H), 7.65-7.85 (m,5H), 4.99 (s, 2H), 4.27 (q, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H).

Step 5: Preparation of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-ethyloxime

To 3.00 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]phthalimide in 30ml of ethanol, 793 mg of hydrazine monohydrate was added, and themixture was stirred at 70° C. for 3 hours. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 100 ml of water and extracted with ethyl acetate (100 ml×2).The resulting organic layers were combined, washed with water (100 ml×1)and dried over saturated aqueous sodium chloride and then anhydroussodium sulfate, and the solvent was evaporated under reduced pressure toobtain 1.62 g of the desired crude product as a brown oil. The oil wasused in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 and 8.48 (d, J=2.0 Hz, 1H), 7.79and 7.77 (d, J=2.0 Hz, 1H), 4.27 and 4.13 (q, J=6.9 Hz, 2H), 3.90 and3.74 (s, 2H), 1.34 and 1.21 (t, J=6.9 Hz, 3H).

Step 6: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-003 of the present invention)

To a solution of 200 mg of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-β-ethyloxime and 90 mg oftriethylamine in 3 ml of dichloromethane, 169 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 30 minutes. After completion of thereaction, the reaction mixture was mixed with 10 ml of water andextracted with ethyl acetate (15 ml×1), the resulting organic layer waswashed with water (10 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 190 mg of thedesired product as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.45 and 8.29 (d, J=2.1 Hz, 1H), 7.80and 7.78 (d, J=2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.52 (bs, 1H), 4.75 and4.52 (d, J=6.0 Hz, 2H), 4.30 and 4.13 (q, J=7.2 Hz, 2H), 1.35 and 1.21(t, J=7.2 Hz, 3H).

Step 7: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

190 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamidewas dissolved in 4 ml of acetonitrile, and the solution was irradiatedwith light for 2.5 hours in a quartz cell (manufactured by Fine, 4 clearwindows for spectroscopy) using a 100 W high-pressure mercury lamp(manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B).After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 41.3 mg of the desired productas white crystals.

m.p.: 84.0 to 86.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 (d, J=2.1 Hz, 1H), 7.79 (d, J=2.1Hz, 1H), 7.5-7.75 (m, 4H), 6.50 (bs, 1H), 4.53 (d, J=4.8 Hz, 2H), 4.13(q, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H).

Synthetic Example 3N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide(Compound No. 17-004 of the present invention)

To 176 mg of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in1 ml of dichloromethane, 10 mg of N,N-dimethylformamide and 381 mg ofoxalyl chloride were added, and the mixture was stirred at roomtemperature for 1 hour. After completion of the reaction, the solventwas evaporated under reduced pressure, and the resulting residue wasdissolved in 2 ml of dichloromethane, and to the solution, 190 mg of the2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-ethyloxime prepared inStep 5 in Synthetic Example 2 in 2 ml of dichloromethane and then 91 mgof pyridine were added dropwise with stirring under cooling with ice,and after the addition, the mixture was stirred at room temperature foranother 2 hours. After completion of the reaction, the reaction mixturewas mixed with 10 ml of water and extracted with chloroform (20 ml×1),the resulting organic layer was washed with water (10 ml×1) and driedover saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:4 to 1:1) as the eluentto obtain 165.3 mg of a pale yellow resinous substance. The resinoussubstance was dissolved in 5 ml of acetic acid and stirred at 70° C. for2 hours, the solvent was evaporated under reduced pressure, and theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:4 to 1:1) as the eluentto obtain 130.6 mg of the desired product as a colorless resinoussubstance (E/Z=1/1).

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.47 (d, J=2.1 Hz, 1H), 7.90and 7.86 (s, 1H), 7.76 and 7.75 (d, J=2.1 Hz, 1H), 6.9-7.1 (m, 1H), 6.84and 6.73 (t, J=54.3 Hz, 1H), 4.71 and 4.49 (d, J=6.0 Hz, 2H), 4.31 and4.14 (q, J=7.2 Hz, 2H), 3.92 and 3.89 (s, 3H), 1.36 and 1.23 (t, J=7.2Hz, 3H).

Synthetic Example 4N-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]-3-(trifluoromethyl)pyrazine-2-carboxamide(Compounds Nos. 9-005 and 9-006 of the present invention) Step 1:Preparation of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanoneoxime

To 2.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone preparedin Step 2 in Synthetic Example 2 in 15 ml of ethanol, 517 mg ofhydroxylamine hydrochloride was added, and the mixture was stirred atroom temperature for 12 hours. After completion of the reaction, thereaction mixture was mixed with 100 ml of water and extracted with ethylacetate (50 ml×2), the resulting organic layers were combined, washedwith water (20 ml×1) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 1.31 g of the desired productas a pale orange oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.53 and 8.50 (d, J=2.1 Hz, 1H), 7.82and 7.81 (d, J=2.1 Hz, 1H), 4.75 and 4.58 (s, 2H).

Step 2: Preparation of2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime

To a solution of 1.31 g of2-bromo-1-(3,5-dichloropyridin-2-yl)ethanoneoxime and 1.71 g oftert-butanol in 20 ml of dichloromethane, 3.27 g of boron trifluoridediethyl ether complex was added, and the mixture was stirred at roomtemperature for 48 hours. After completion of the reaction, the solventwas evaporated under reduced pressure, and the resulting residue waspurified by silica gel column chromatography using ethyl acetate-hexane(with a gradient of from 0:100 to 15:85) as the eluent to obtain 140 mgof the desired product as a colorless oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.48 (d, J=2.1 Hz, 1H), 7.81and 7.77 (d, J=2.1 Hz, 1H), 4.70 and 4.53 (s, 2H), 1.39 and 1.38 (s,9H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]phthalimide

To 140 mg of2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime in 2 mlof N,N-dimethylformamide, 91 mg of potassium phthalimide was added, andthe mixture was stirred at room temperature for 5 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 10 ml ofwater and extracted with ethyl acetate (15 ml×1), the resulting organiclayer was washed with water (10 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 2:8 to 4:6) as the eluent to obtain 162 mg of thedesired product as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.30 (d, J=2.1 Hz, 1H), 7.7-7.85 (m,2H), 7.74 (d, J=2.1 Hz, 1H), 7.6-7.7 (m, 2H), 4.97 (s, 2H), 1.27 (s,9H).

Step 4: Preparation of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime

To 162 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]phthalimide in10 ml of ethanol, 40 mg of hydrazine monohydrate was added, and themixture was stirred at 80° C. for 1 hour. After completion of thereaction, the solvent was evaporated under reduced pressure, and thereaction mixture was mixed with 30 ml of water and extracted with ethylacetate (25 ml×2). The resulting organic layers were combined, washedwith water (20 ml×1) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure to obtain 89 mg of the desired crude product as acolorless oil. The oil was used in the next step without furtherpurification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.47 (d, J=2.4 Hz, 1H), 7.79 (d, J=2.4Hz, 1H), 3.88 (bs, 2H), 1.36 (s, 9H).

Step 5: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]-3-(trifluoromethyl)pyrazine-2-carboxamide

To 74 mg of 3-(trifluoromethyl)pyrazine-2-carboxylic acid in 3 ml ofdichloromethane, 10 mg of N,N-dimethylformamide and 57 mg of oxalylchloride were added, and the mixture was stirred at room temperature for1 hour. After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was dissolved in 10 mlof dichloromethane. To the solution, 89 mg of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime and 39mg of triethylamine were added with stirring under cooling with ice, andthe mixture was stirred at room temperature for another 1 hour. Aftercompletion of the reaction, the reaction mixture was mixed with 10 ml ofwater and extracted with chloroform (10 ml×1), the resulting organiclayer was dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 1:9to 3:7) as the eluent to obtain 22 mg of geometrical isomer A and 111 mgof geometrical isomer B of the desired product as colorless resinoussubstances.

Isomer A:

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.77 (d, J=2.4 Hz, 1H), 8.69 (d, J=2.4Hz, 1H), 8.46 (d, J=2.1 Hz, 1H), 8.14 (bs, 1H), 7.78 (d, J=2.1 Hz, 1H),4.77 (d, J=6.0 Hz, 2H), 1.42 (s, 9H).

Isomer B:

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.77 (d, J=2.4 Hz, 1H), 8.70 (d, J=2.4Hz, 1H), 8.46 (d, J=2.1 Hz, 1H), 8.17 (bs, 1H), 7.78 (d, J=2.1 Hz, 1H),4.79 (d, J=6.0 Hz, 2H), 1.39 (s, 9H).

Synthetic Example 5(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-126 of the present invention) Step 1: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide

To 3.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone preparedin Step 2 in Synthetic Example 2 in 30 ml of N,N-dimethylformamide, 4.13g of potassium phthalimide was added, and the mixture was stirred at 80°C. for 3 hours and then at room temperature for 18 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 150 mlof water and extracted with ethyl acetate (50 ml×2), the resultingorganic layers were combined, washed with water (50 ml×1) and dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure. The resulting residuewas mixed with 40 ml of a mixture of diisopropyl ether and hexane (1:1),the insolubles were filtered off, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 15:85 to 25:75) as the eluent to obtain 0.32 g of the desiredproduct as a dark brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.58 (d, J=2.0 Hz, 1H), 7.65-7.8 (m,5H), 5.30 (s, 2H).

Step 2: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimide

To 0.32 g of N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimide in15 ml of ethanol, 0.66 g of hydroxylamine hydrochloride was added andrefluxed with heating for 4 hours with stirring. After completion of thereaction, the solvent was evaporated under reduced pressure, and thereaction mixture was mixed with 30 ml of water and 50 ml of ethylacetate, and the resulting organic layer was collected. The organiclayer was washed with water (30 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, the solvent wasevaporated under reduced pressure, and the resulting residue was washedwith 10 ml of hexane to obtain 265 mg of the desired product as yellowcrystals.

m.p.: 138.0 to 141.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.47 and 8.30 (d, J=2.0 Hz, 1H), 8.13and 7.52 (s, 1H), 7.65-7.9 (m, 5H), 5.05 and 4.78 (s, 2H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimide

To 265 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimide in 2ml of N,N-dimethylformamide, 310 mg of potassium carbonate and 387 mg of1-iodopropane were added, and the mixture was stirred at roomtemperature for 18 hours. After completion of the reaction, the reactionmixture was mixed with 30 ml of water and extracted with ethyl acetate(50 ml×1), the resulting organic layer was washed with water (50 ml×1)and dried over saturated aqueous sodium chloride and then anhydroussodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 15:85 to 25:75) asthe eluent to obtain 235 mg of the desired product as a yellow resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.42 and 8.29 (d, J=2.0 Hz, 1H),7.65-7.9 (m, 5H), 4.99 and 4.76 (s, 2H), 4.18 and 4.00 (t, J=6.7 Hz,2H), 1.5-1.75 (m, 2H), 0.93 and 0.81 (t, J=7.5 Hz, 3H).

Step 4: Preparation of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-propyloxime

To 235 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimide in 5ml of ethanol, 90 mg of hydrazine monohydrate was added and refluxedwith heating for 3 hours with stirring. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 20 ml of water and extracted with ethyl acetate (35 ml×2).The resulting organic layers were combined, washed with water (20 ml×1)and dried over saturated aqueous sodium chloride and then anhydroussodium sulfate, and the solvent was evaporated under reduced pressure toobtain 151 mg of the desired crude product as a brown oil. The oil wasused in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 and 8.48 (d, J=2.0 Hz, 1H), 7.78and 7.76 (d, J=2.0 Hz, 1H), 4.17 and 4.01 (t, J=6.6 Hz, 2H), 3.89 and3.73 (s, 2H), 1.5-1.85 (m, 2H), 0.98 and 0.86 (t, J=7.4 Hz, 3H).

Step 5: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-004 of the present invention)

In a solution of 151 mg of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-propyloxime and 86 mg oftriethylamine in 4 ml of dichloromethane, 154 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 2 hours. After completion of thereaction, the reaction mixture was mixed with 10 ml of water andextracted with chloroform (30 ml×1), the resulting organic layer waswashed with water (10 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 2:8 to 3:7) as the eluent to obtain 218 mg of thedesired product as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 and 8.44 (d, J=2.1 Hz, 1H), 7.80and 7.78 (d, J=2.1 Hz, 1H), 7.35-7.7 (m, 4H), 6.53 and 6.49 (bs, 1H),4.75 and 4.52 (d, J=6.3 Hz, 2H), 4.21 and 4.03 (t, J=6.9 Hz, 2H),1.7-1.8 and 1.55-4.65 (m, 2H), 0.96 and 0.86 (t, J=7.5 Hz, 3H).

Step 6: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 218 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 3 ml of acetonitrile, 5 mg of benzophenone was added, and the mixturewas irradiated with light for 48 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supplyUM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 25:75 to 35:65) as the eluent to obtain 83 mg of the desiredproduct as white crystals.

m.p.: 80.0 to 83.0° C.

¹H NMR (CDCl₃, Me_(a)Si, 300 MHz) δ8.51 (d, J=1.9 Hz, 1H), 7.79 (d,J=1.9 Hz, 1H), 7.5-7.75 (m, 4H), 6.50 (bs, 1H), 4.53 (d, J=5.2 Hz, 2H),4.04 (t, J=6.6 Hz, 2H), 1.5-1.7 (m, 2H), 0.86 (t, J=7.4 Hz, 3H)

Synthetic Example 6(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-024 of the present invention) Step 1: Preparation of2-bromo-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone

To 0.82 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone in 10ml of tetrahydrofuran, 1.38 g of trimethylphenylammonium tribromide wasadded, and the mixture was stirred at room temperature for 16 hours.After completion of the reaction, the precipitated solid was filteredoff through celite, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using diethyl ether as the eluent to obtain 1.43 g of thedesired product as a brown oil. The oil was used in the next stepwithout further purification.

Step 2: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide

To 1.43 g of2-bromo-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone in 10 ml ofN,N-dimethylformamide, 0.68 g of potassium phthalimide and 0.01 g ofpotassium iodide were added, and the mixture was stirred at 85° C. for 1hour. After completion of the reaction, the reaction mixture was allowedto cool to room temperature, mixed with 10 ml of water and extractedwith ethyl acetate (10 ml×3), the resulting organic layers werecombined, washed with water and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bypreparative medium pressure liquid chromatography (preparative mediumpressure chromatograph: YFLC-Wprep manufactured by Yamazen Science,Inc.) using ethyl acetate-hexane (with a gradient of from 5:95 to 46:60)as the eluent to obtain 0.47 g of the desired product as a pale yellowresinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.87 (d, J=1.8 Hz, 1H), 8.10 (d, J=1.8Hz, 1H), 7.85-7.95 (m, 2H), 7.7-7.8 (m, 2H), 5.32 (s, 2H).

Step 3: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]phthalimide

To a solution of 0.47 g ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimideand 0.54 g of hydroxylamine hydrochloride in 5 ml of ethanol, 0.94 g ofpyridine was added, and the mixture was stirred at room temperature for24 hours. After completion of the reaction, the reaction mixture wasmixed with 5 ml of water and extracted with ethyl acetate (5 ml×3), theresulting organic layers were combined, dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasdistilled off under reduced pressure. The resulting residue was purifiedby preparative medium pressure liquid chromatography (preparative mediumpressure chromatograph: YFLC-Wprep manufactured by Yamazen Science,Inc.) using ethyl acetate-hexane (with a gradient of from 1:3 to 2:2) asthe eluent to obtain 325 mg of the desired product as white crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ10.57 and 9.75 (s, 1H), 8.7-8.8 (m, 1H),7.9-7.95 (m, 1H), 7.6-7.85 (m, 4H), 5.07 and 4.80 (s, 2H)

Step 4: Preparation of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]phthalimide

To 300 mg ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]phthalimidein 5 ml of N,N-dimethylformamide, 324 mg of potassium carbonate and 158mg of cyclopropylmethyl bromide were added, and the mixture was stirredat room temperature for 18 hours. After completion of the reaction, thereaction mixture was mixed with 5 ml of water and extracted with ethylacetate (5 ml×3), the resulting organic layers were combined, washedwith water and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by preparative mediumpressure liquid chromatography (preparative medium pressurechromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) usingethyl acetate-hexane (with a gradient of from 1:19 to 4:16) as theeluent to obtain 98 mg of the desired product as a pale yellow resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.61 (d, J=1.5 Hz, 1H), 7.97 (d, J=1.5Hz, 1H), 7.75-7.85 (m, 2H), 7.65-7.75 (m, 2H), 5.03 (s, 2H), 4.03 (d,J=7.5 Hz, 2H), 1.05-1.25 (m, 1H), 0.4-0.5 (m, 2H), 0.15-0.25 (m, 2H).

Step 5: Preparation of(E)-2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-(cyclopropylmethyl)oxime

To 98 mg of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]phthalimidein 3 ml of ethanol, 76 mg of hydrazine monohydrate was added, and themixture was stirred at 80° C. for 1 hour. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3). Theresulting organic layers were combined, dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using methanol-chloroform (1:10) as theeluent to obtain 65 mg of the desired product as a pale yellow oil. Theoil was used in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.78 (d, J=1.5 Hz, 1H), 8.00 (d, J=1.5Hz, 1H), 4.05 (d, J=7.2 Hz, 2H), 3.96 (s, 2H), 1.66 (bs, 2H), 1.15-1.35(m, 1H), 0.55-0.65 (m, 2H), 0.3-0.4 (m, 2H).

Step 6: Preparation of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-023 of the present invention)

In a solution of 65 mg of(E)-2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-(cyclopropylmethyl)oximeand 32 mg of triethylamine in 2 ml of dichloromethane, 39 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 2 ml of water andextracted with dichloromethane (2 ml×1), the resulting organic layer wasdried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by preparative medium pressure liquidchromatography (preparative medium pressure chromatograph: YFLC-Wprepmanufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (witha gradient of from 2:18 to 5:15) as the eluent to obtain 85 mg of thedesired product as white crystals.

m.p.: 98.0 to 101.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.75 (d, J=1.5 Hz, 1H), 8.02 (d, J=1.5Hz, 1H), 7.6-7.7 (m, 1H), 7.45-7.6 (m, 2H), 7.35-7.45 (m, 1H), 6.55 (bs,1H), 4.81 (d, J=6.0 Hz, 2H), 4.19 (d, J=7.2 Hz, 2H), 1.15-1.3 (m, 1H),0.3-0.4 (m, 2H), 0.5-0.6 (m, 2H).

Step 7: Preparation of(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 85 mg of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 3 ml of acetonitrile, 1 mg of benzophenone was added, and the mixturewas irradiated with light for 5 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 5:5) as the eluent to obtain 47 mg of the desired product aswhite crystals.

m.p.: 73.0 to 74.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.80 (d, J=1.5 Hz, 1H), 8.01 (d, J=1.5Hz, 1H), 7.65-7.75 (m, 1H), 7.5-7.65 (m, 3H), 6.52 (bs, 1H), 4.58 (d,J=6.0 Hz, 2H), 3.91 (d, J=7.2 Hz, 2H), 1.0-1.15 (m, 1H), 0.45-0.55 (m,2H), 0.2-0.3 (m, 2H).

Synthetic Example 7(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-117 of the present invention) Step 1: Preparation of1-(3,5-dichloropyridin-2-yl)-1-propanone

To 5.0 g of 3,5-dichloropyridin-2-carbonitrile in 50 ml oftetrahydrofuran, 38 ml of 13% ethylmagnesium bromide in tetrahydrofuranwas added dropwise with stirring under cooling with ice, and after theaddition, the mixture was stirred at room temperature for 1 hour. Aftercompletion of the reaction, the reaction mixture was added dropwise to55 ml of 1N aqueous hydrochloric acid with stirring under cooling withice, and extracted with ethyl acetate (50 ml×2). The resulting organiclayers were combined, washed with water (50 ml×1) and dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure. The resulting residuewas purified by silica gel column chromatography using ethylacetate-hexane (with a gradient of 5:95 to 15:85) as the eluent toobtain 4.4 g of the desired product as pale yellow crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.48 (d, J=2.1 Hz, 1H), 7.81 (d, J=2.1Hz, 1H), 3.10 (q, J=7.2 Hz, 2H), 1.20 (t, J=7.2 Hz, 3H).

Step 2: Preparation of 2-bromo-1-(3,5-dichloropyridin-2-yl)-1-propanone

To 4.40 g of 1-(3,5-dichloropyridin-2-yl)-1-propanone in 20 ml of ethylacetate-chloroform (1:1), 10.12 g of copper(I) bromide was added, andthe mixture was stirred at room temperature for 12 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 30 ml ofsaturated aqueous sodium hydrogencarbonate, and the precipitated solidwas filtered off through celite and washed with 20 ml of ethyl acetate.The filtrate was mixed with 100 ml of ethyl acetate, the resultingorganic layer was collected, washed with water (30 ml×1) and dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure. The resulting residuewas purified by silica gel column chromatography using ethylacetate-hexane (with a gradient of from 5:95 to 15:85) as the eluent toobtain 5.00 g of the desired product as a pale orange oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 (d, J=2.1 Hz, 1H), 7.86 (d, J=2.1Hz, 1H), 5.76 (q, J=6.9 Hz, 1H), 1.89 (d, J=6.9 Hz, 3H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl)phthalimide

To 5.00 g of 2-bromo-1-(3,5-dichloropyridin-2-yl)-1-propanone in 20 mlof N,N-dimethylformamide, 3.27 g of potassium phthalimide was added, andthe mixture was stirred at room temperature for 2 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 50 ml ofwater and extracted with ethyl acetate (50 ml×2), and the resultingorganic layers were combined, washed with water (30 ml×1) and dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure to obtain 2.02 g ofthe desired crude product as brown crystals. The crystals were used inthe next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.34 (d, J=2.1 Hz, 1H), 7.65-7.9 (m,5H), 5.57 (q, J=6.9 Hz, 1H), 1.68 (d, J=6.9 Hz, 3H).

Step 4: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]phthalimide

To 1.00 g ofN-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl]phthalimide in 10 mlof ethanol, 2.39 g of methoxyamine hydrochloride and 3.40 g of pyridinewere added and refluxed with heating for 18 hours with stirring. Aftercompletion of the reaction, the reaction mixture was allowed to cool toroom temperature, mixed with 30 ml of 1N aqueous hydrochloric acid andextracted with ethyl acetate (40 ml×2). The resulting organic layerswere combined, washed with 30 ml of 1N aqueous hydrochloric acid anddried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluentto obtain 0.81 g of the desired product as a colorless resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.34 and 8.20 (bs, 1H), 7.65-7.85 (m,5H), 5.95-6.05 and 5.3-5.65 (m, 1H), 4.01 and 3.86 (bs, 3H), 1.75-1.85(m, 3H).

Step 5: Preparation of2-amino-1-(3,5-dichloropyridin-2-yl)-1-propanone-O-methyloxime

To 810 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-methoxyinnino-1-methylethyl]phthalimidein 30 ml of ethanol, 161 mg of hydrazine monohydrate was added andrefluxed with heating for 1 hour with stirring. After completion of thereaction, the solvent was evaporated under reduced pressure, and theresulting residue was mixed with 20 ml of water and extracted with ethylacetate (30 ml×1). The resulting organic layer was washed with water (20ml×1) and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure to obtain 430 mg of the desired crude product as a pale yellowoil. The oil was used in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 and 8.48 (d, J=2.1 Hz, 1H), 7.79and 7.77 (d, J=2.1 Hz, 1H), 4.4-4.5 and 3.9-3.05 (m, 1H), 3.99 and 3.84(s, 3H), 1.32 and 1.27 (d, J=6.9 Hz, 3H).

Step 6: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-115 of the present invention)

To a solution of 430 mg of2-amino-1-(3,5-dichloropyridin-2-yl)-1-propanone-β-methyloxime and 210mg of triethylamine in 20 ml of dichloromethane, 361 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 30 ml of water andextracted with chloroform (20 ml×1), the resulting organic layer waswashed with water (20 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 296 mg of thedesired product as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.41 (d, J=1.8 Hz, 1H), 7.82and 7.79 (d, J=1.8 Hz, 1H), 7.4-7.75 (m, 4H), 6.65-7.0 (m, 1H), 5.7-5.85and 5.2-5.3 (m, 1H), 4.05 and 3.87 (s, 3H), 1.56 and 1.45 (d, J=6.6 Hz,3H).

Step 7: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamide

160 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-methoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamidein 4 ml of acetonitrile was irradiated with light for 12 hours in aquartz cell (manufactured by Fine, 4 clear windows for spectroscopy)using a 100 W high-pressure mercury lamp (manufactured by USHIO INC.,lamp: UM-102, power supply: UM-103B-B). After completion of thereaction, the solvent was evaporated under reduced pressure, and theprecipitated solid was washed with 5 ml of diisopropyl ether to obtain33 mg of the desired product as white crystals.

m.p.: 104.0 to 105.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.80 (d, J=2.1Hz, 1H), 7.5-7.75 (m, 4H), 6.78 (bs, 1H), 5.2-5.35 (m, 1H), 3.87 (s,3H), 1.45 (d, J=6.6 Hz, 3H).

Synthetic Example 8

(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-185 of the present invention)

Step 1: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]phthalimide

To 214 mg of theN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimideprepared in Step 2 in Synthetic Example 6 in 3 ml of ethanol, 84 mg ofethoxyamine hydrochloride was added, and the mixture was stirred at roomtemperature for 18 hours. After completion of the reaction, the reactionmixture was mixed with 5 ml of water and extracted with ethyl acetate (5ml×3), and the resulting organic layers were combined, dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure. The resulting residuewas purified by preparative medium pressure liquid chromatography(preparative medium pressure chromatograph: YFLC-Wprep manufactured byYamazen Science, Inc.) using ethyl acetate-hexane (with a gradient offrom 2:18 to 5:15) as the eluent to obtain 111 mg of the desired productas a brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.60 (d, J=1.5 Hz, 1H), 7.97 (d, J=1.5Hz, 1H), 7.8-7.9 (m, 2H), 7.65-7.75 (m, 2H), 5.02 and 4.80 (s, 2H), 4.29and 4.11 (q, J=7.2 Hz, 2H), 1.30 and 1.17 (t, J=7.2 Hz, 3H).

Step 2: Preparation of2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-ethyloxime

To 111 mg ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]phthalimidein 3 ml of ethanol, 86 mg of hydrazine monohydrate was added, and themixture was stirred at 80° C. for 1 hour. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3). Theresulting organic layers were combined, dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, the solvent wasevaporated under reduced pressure, and the resulting residue waspurified by silica gel column chromatography using methanol-chloroform(1:10) as the eluent to obtain 47 mg of the desired product as a yellowoil. The oil was used in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.80 and 8.77 (d, J=1.5 Hz, 1H), 8.00and 7.97 (d, J=1.5 Hz, 1H), 4.29 and 4.13 (q, J=7.2 Hz, 2H), 3.93 and3.77 (s, 2H), 1.70 (bs, 2H), 1.35 and 1.22 (t, J=7.2z, 3H).

Step 3: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-016 of the present invention)

To a solution of 47 mg of2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-ethyloximeand 25 mg of triethylamine in 2 ml of dichloromethane, 31 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 2 ml of water andextracted with dichloromethane (2 ml×1), the resulting organic layer wasdried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by preparative medium pressure liquidchromatography (preparative medium pressure chromatograph: YFLC-Wprepmanufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (witha gradient of from 2:18 to 5:15) as the eluent to obtain 48 mg of thedesired product as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.81 and 8.75 (d, J=1.5 Hz, 1H), 8.03and 8.00 (d, J=1.5 Hz, 1H), 7.35-7.55 (m, 4H), 6.51 (bs, 1H), 4.79 and4.58 (d, J=5.4 Hz, 2H), 4.34 and 4.16 (q, J=7.2 Hz, 2H), 1.38 and 1.24(t, J=7.2 Hz, 3H).

Step 4: Preparation of(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 48 mg ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 3 ml of acetonitrile, 1 mg of benzophenone was added, and the mixturewas irradiated with light for 4 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 5:5) as the eluent to obtain 42 mg of the desired product aswhite crystals.

m.p.: 60.0 to 62.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.81 (d, J=1.5 Hz, 1H), 8.00 (d, J=1.5Hz, 1H), 7.5-7.55 (m, 4H), 6.51 (bs, 1H), 4.79 (d, J=5.4 Hz, 2H), 4.16(q, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H).

Synthetic Example 9N-[2-(3-chloro-5-methoxypyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide(compound No. 2-083 of the present invention) Step 1: Preparation of2-bromo-1-(3-chloro-5-methoxypyridin-2-yl)ethanone

To 0.90 g of 1-(3-chloro-5-methoxypyridin-2-yl)ethanone in 10 ml oftetrahydrofuran, 1.82 g of trimethylphenylammonium tribromide was added,and the mixture was stirred at room temperature for 16 hours. Aftercompletion of the reaction, the precipitated solid was filtered off, andthe solvent was evaporated under reduced pressure. The resulting residuewas purified by silica gel column chromatography using ethylacetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent toobtain 0.57 g of the desired product as pale yellow crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.23 (d, J=2.4 Hz, 1H), 7.28 (d, J=2.4Hz, 1H), 4.74 (s, 2H), 3.95 (s, 3H).

Step 2: Preparation ofN-[2-(3-chloro-5-methoxypyridin-2-yl)-2-oxoethyl]phthalimide

To 570 mg of 2-bromo-1-(3-chloro-5-methoxypyridin-2-yl)ethanone in 10 mlof N,N-dimethylformamide, 800 mg of potassium phthalimide and 36 mg ofpotassium iodide were added, and the mixture was stirred at 80° C. for 5hours. After completion of the reaction, the reaction mixture wasallowed to cool to room temperature, mixed with 20 ml of water andextracted with ethyl acetate (40 ml×1), the resulting organic layer wasdried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluentto obtain 0.12 g of the desired product as white crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.30 (d, J=2.4 Hz, 1H), 7.85-7.95 (m,2H), 7.7-7.8 (m, 2H), 7.27 (d, J=2.4 Hz, 2H), 5.31 (s, 2H), 3.96 (s,3H).

Step 3: Preparation ofN-[2-(3-chloro-5-methoxypyridin-2-yl)-2-(methoxyimino)ethyl]phthalimide

To a solution of 120 mg ofN-[2-(3-chloro-5-methoxypyridin-2-yl)-2-oxoethyl]phthalimide and 60 mgof methoxyamine hydrochloride in 5 ml of ethanol, 85 mg of pyridine wasadded, and the mixture was stirred at 80° C. for 6 hours. Aftercompletion of the reaction, the solvent was evaporated under reducedpressure, and the resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 1:9to 3:7) as the eluent to obtain 101 mg of the desired product as a paleyellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.17 and 8.01 (d, J=2.7 Hz, 1H),7.65-7.9 (m, 4H), 7.20 and 7.19 (d, J=2.7 Hz, 1H), 4.99 and 4.77 (s,2H), 4.04 and 3.84 (s, 3H), 3.84 and 3.78 (s, 3H).

Step 4: Preparation ofN12-(3-chloro-5-methoxypyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 101 mg ofN-[2-(3-chloro-5-methoxypyridin-2-yl)-2-(methoxyimino)ethyl]phthalimidein 5 ml of ethanol, 42 mg of hydrazine monohydrate was added, and themixture was stirred at room temperature for 12 hours. After completionof the reaction, the reaction mixture was mixed with 15 ml of water andextracted with ethyl acetate (30 ml×1), the resulting organic layer waswashed with water (20 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was dissolvedin 5 ml of dichloromethane, and to the solution, 46 mg of2-(trifluoromethyl)benzoyl chloride and then 33 mg of triethylamine wereadded, and the mixture was stirred at room temperature for one hour.After completion of the reaction, the reaction mixture was mixed with 5ml of water and extracted with ethyl acetate (15 ml×1), the resultingorganic layer was washed with water (20 ml×1) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waspurified by silica gel column chromatography using ethyl acetate-hexane(with a gradient of from 1:9 to 3:7) as the eluent to obtain 87 mg of apale yellow resinous substance. The resinous substance was dissolved in5 ml of ethanol, and 0.5 ml of a 1,4-dioxane solution (4 mol/L) ofhydrogen chloride, and the mixture was stirred at 70° C. for 2 hours.The solvent was evaporated under reduced pressure, and the resultingresidue was purified by silica gel column chromatography using ethylacetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent toobtain 80 mg of the desired product as a colorless resinous substance(E/Z=55/45).

¹H NMR (CDCl₃, Me_(a)Si, 300 MHz) δ8.23 and 8.19 (d, J=2.7 Hz, 1H),7.35-7.75 (m, 4H), 7.28 and 7.27 (d, J=2.7 Hz, 1H), 6.57 and 6.50 (bs,1H), 4.74 and 4.52 (d, J=6.0 Hz, 2H), 4.05 and 3.87 (s, 3H), 3.84 (bs,3H).

Synthetic Example 10

(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-128 of the present invention)

Step 1: Preparation of1-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-1,3,5,7-tetraazatricyclo[3,3,1,1^(3,7)]decan-1-iumbromide

5.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone prepared inStep 2 in Synthetic Example 2 in 30 ml of chloroform was added dropwiseto 2.61 g of 1,3,5,7-tetraazatricyclo[3,3,1,1^(3,7)]decane in 50 ml ofchloroform with stirring at room temperature, and the mixture wasstirred at the same temperature for 2 hours. After completion of thereaction, the precipitated crystals were collected by filtration andwashed with 30 ml of chloroform to obtain 7.40 g of the desired productas white crystals.

m.p.>177.0° C. (decomposition)

Step 2: Preparation of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanonehydrochloride

To a suspension of 7.0 g of1-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-1,3,5,7-tetraazatricyclo[3,3,1,1^(3,7)]decan-1-iumbromide in 70 ml of ethanol, 7 ml of concentrated hydrochloric acid wasadded, and the mixture was stirred at room temperature for 14 hours.After completion of the reaction, the solid was collected by filtrationand washed with 15 ml of ethanol to obtain 3.7 g of the desired productas white crystals.

m.p.>207.0° C. (decomposition)

¹H NMR (CDCl₃, Me₄Si-DMSO-d₆, 300 MHz) δ8.83 (bs, 1H), 8.51 (bs, 1H),4.54 (bs, 2H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide

To a suspension of 3.7 g of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanonehydrochloride in 50 ml of ethyl acetate, 30 ml of water and 3.5 g of2-(trifluoromethyl)benzoyl chloride were added, and 6.1 g of potassiumcarbonate in 30 ml of water was added dropwise with stirring undercooling with ice, and the mixture was stirred at the same temperaturefor 30 minutes. After completion of the reaction, the reaction mixturewas mixed with 20 ml of ethyl acetate, the resulting organic layer wascollected, washed with water (20 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 2:8 to 6:4) as the eluent to obtain 3.8 g of thedesired product as pale yellow crystals.

m.p.: 123.0 to 125.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.55 (d, J=2.1 Hz, 1H), 7.88 (d, J=2.1Hz, 1H), 7.5-7.75 (m, 4H), 6.69 (bs, 1H), 5.10 (d, J=4.8 Hz, 2H).

Step 4: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a solution of 3.38 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamideand 0.934 g of hydroxylamine hydrochloride in 20 ml of ethanol, 1.10 gof sodium acetate was added, and the mixture was stirred at roomtemperature for 12 hours. After completion of the reaction, the solventwas evaporated under reduced pressure, the resulting residue was mixedwith 40 ml of water and extracted with ethyl acetate (20 ml×2), theresulting organic layers were combined, washed with water (20 ml×1) anddried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 2:8 to 4:6) as the eluentto obtain 1.90 g of the desired product as white crystals.

m.p.: 134.0 to 136.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.45 (d, J=2.4 Hz, 1H), 7.81and 7.80 (d, J=2.4 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 (bs, 1H), 4.80 and4.55 (d, J=6.3 Hz, 2H).

Step 5: Preparation of(E)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-239 of the present invention)

To a suspension of 300 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 315 mg of potassium carbonate in 3 ml of N,N-dimethylformamide, 195mg of 2-iodopropane was added, and the mixture was stirred at roomtemperature for 6 hours. After completion of the reaction, the reactionmixture was mixed with 20 ml of water and extracted with ethyl acetate(10 ml×2), the resulting organic layers were combined, washed with water(10 ml×2), the resulting organic layer was dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 258 mg of thedesired product as white crystals.

m.p.: 54.0 to 57.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.45 (d, J=2.1 Hz, 1H), 7.81 (d, J=2.1Hz, 1H), 7.35-7.7 (m, 4H), 6.49 (bs, 1H), 4.76 (d, J=6.3 Hz, 2H),4.45-4.6 (m, 1H), 1.33 (d, J=6.0 Hz, 6H).

Step 6: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 258 mg of(E)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 4 ml of acetonitrile, 2 mg of benzophenone was added, and the mixturewas irradiated with light for 12 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 231 mg of the desired productas white crystals.

m.p.: 107.0 to 108.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.78 (d, J=2.1Hz, 1H), 7.5-7.8 (m, 4H), 6.54 (bs, 1H), 4.53 (d, J=5.1 Hz, 2H),4.3-4.45 (m, 1H), 1.18 (d, J=6.3 Hz, 6H).

Synthetic Example 11

(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]2-(trifluoromethyl)benzamide(compound No. 2-140 of the present invention)

Step 1: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide(compound No. 2-139 of the present invention)

To a solution of 200 mg of theN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamideprepared in Step 3 in Synthetic Example 10 and 199 mg ofO-(tert-butyl)hydroxylamine hydrochloride in 2.6 ml of ethanol, 167 mgof pyridine was added, and the mixture was stirred at 70° C. for 18hours. After completion of the reaction, the solvent was evaporatedunder reduced pressure, the resulting residue was mixed with 2 ml ofwater and extracted with ethyl acetate (2 ml×2), the resulting organiclayers were combined, dried over saturated aqueous sodium chloride andthen anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 50:50) as the eluent to obtain 207 mg of the desiredproduct as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.44 (d, J=2.4 Hz, 1H),7.25-7.85 (m, 5H), 6.54 (bs, 1H), 4.77 and 4.54 (d, J=5.7 Hz, 2H), 1.37and 1.24 (s, 9H).

Step 2: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide

207 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(tert-butoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 4 ml of acetonitrile was irradiated with light for 8 hours in aquartz cell (manufactured by Fine, 4 clear windows for spectroscopy)using a 100 W high-pressure mercury lamp (manufactured by USHIO INC.,lamp: UM-102, power supply: UM-103B-B). After completion of thereaction, the solvent was evaporated under reduced pressure, and theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:9 to 5:5) to obtain 190mg of the desired product as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.0 Hz, 1H), 7.77 (d, J=2.0Hz, 1H), 7.5-7.75 (m, 4H), 6.56 (bs, 1H), 4.53 (d, J=5.1 Hz, 2H), 1.24(s, 9H).

Synthetic Example 12

(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(compound No. 2-212 of the present invention)

Step 1: Preparation of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]carbamate

To 35.1 g of 2-bromo-3,5-dichloropyridine in 10 ml of tetrahydrofuran,116.3 ml of a 1.3 M tetrahydrofuran solution of isopropylmagnesiumchloride-lithium chloride complex was added dropwise with stirring at−20° C., and after the addition, the mixture was stirred at the sametemperature for 15 minutes. Then, to the reaction mixture, 15.0 g ofN-methoxy-N-methyl-2-(tert-butoxycarbonylamino)acetamide in 114 ml oftetrahydrofuran was added dropwise, and after the addition, the mixturewas stirred at the same temperature for another 2 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 100 mlof saturated aqueous ammonium chloride and 100 ml of water and extractedwith ethyl acetate (200 ml×2), the resulting organic layers werecombined, washed with water (100 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 0:10 to 3:7) as the eluent to obtain 12.5 g of thedesired product as pale yellow crystals.

m.p.: 82.0 to 84.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 (d, J=2.1 Hz, 1H), 7.85 (d, J=2.1Hz, 1H), 5.31 (bs, 1H), 4.76 (bs, 2H), 1.47 (s, 9H).

Step 2: Preparation of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate

To a solution of 10.6 g of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]carbamate and 4.8 g ofhydroxylamine hydrochloride in 87 ml of ethanol, 6.1 g of pyridine wasadded, and the mixture was stirred at room temperature for 24 hours.After completion of the reaction, the solvent was evaporated underreduced pressure, the resulting residue was mixed with 50 ml of waterand extracted with ethyl acetate (100 ml×2), the resulting organiclayers were combined, dried over saturated aqueous sodium chloride andthen anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 40:60) as the eluent to obtain 10.1 g of the desiredproduct as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.47 (d, J=2.4 Hz, 1H), 7.82and 7.79 (d, J=2.4 Hz, 1H), 5.65 and 5.16 (bs, 1H), 4.46 and 4.24 (d,J=5.4 Hz, 2H), 1.39 and 1.34 (s, 9H).

Step 3: Preparation of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]carbamate

To 5.0 g of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate in 16.0ml of N,N-dimethylformamide, 4.3 g of potassium carbonate and 5.4 g of2,2,2-trifluoroethyl trifluoromethanesulfonate were added, and themixture was stirred at room temperature for 18 hours. After completionof the reaction, the reaction mixture was mixed with 100 ml of water andextracted with ethyl acetate (100 ml×2), the resulting organic layerswere combined, washed with water (50 ml×2) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waspurified by silica gel column chromatography using ethyl acetate-hexane(with a gradient of from 0:10 to 3:7) as the eluent to obtain 4.8 g ofthe desired product as a pale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 and 8.49 (d, J=1.8 Hz, 1H), 7.80and 7.78 (d, J=1.8 Hz, 1H), 4.94 (bs, 1H), 4.0-4.65 (m, 4H), 1.39 and1.34 (s, 9H).

Step 4: Preparation of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(2,2,2-trifluoroethyl)oximehydrochloride

To 4.9 g of tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]carbamatein 5 ml of 1,4-dioxane, 25 ml of a 1,4-dioxane solution (4 mol/L) ofhydrogen chloride was added, and the mixture was stirred at roomtemperature for 3 hours. After completion of the reaction, the solventwas evaporated under reduced pressure, and the resulting residue waswashed with 20 ml of hexane to obtain 3.1 g of the desired product aspale brown crystals.

m.p.: 141.0 to 143.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.98 (bs, 3H), 8.56 and 8.52 (d, J=2.1Hz, 1H), 7.83 and 7.80 (d, J=2.1 Hz, 1H), 4.72 and 4.54 (q, J=8.7 Hz,2H), 4.28 and 4.10 (bs, 2H).

Step 5: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(compound No. 2-011 of the present invention)

To 2.0 g of2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(2,2,2-trifluoroethyl)oximehydrochloride in 12.0 ml of water, 1.4 g of 2-(trifluoromethyl)benzoylchloride in 12.0 ml of dichloromethane and 2.4 g of potassium carbonatewere added at room temperature with stirring, and the mixture wasstirred at the same temperature for 2 hours. After completion of thereaction, the resulting organic layer was collected and dried overanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 2.6 g of the desired product as a paleyellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 and 8.46 (d, J=2.1 Hz, 1H), 7.82and 7.81 (d, J=2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.39 (bs, 1H), 4.80 and4.57 (d, J=6.0 Hz, 2H), 4.61 and 4.42 (q, J=8.4 Hz, 2H).

Step 6: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

2.6 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamidewas dissolved in 12.0 ml of acetonitrile, and the solution wasirradiated with light for 48 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was washed with 20 mlof hexane to obtain 2.1 g of the desired product as white crystals.

m.p.: 100.0 to 102.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 (d, J=2.1 Hz, 1H), 7.45-7.85 (m,5H), 6.39 (bs, 1H), 4.57 (d, J=5.4 Hz, 2H), 4.42 (q, J=8.7 Hz, 2H).

Synthetic Example 13(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-(Z)-(isopropoxyimino)-1-methylethyl]-2-(trifluoromethyl)benzamide(compound No. 2-132 of the present invention) Step 1: Preparation of(S)—N-methoxy-N-methyl-2-(tert-butoxycarbonylamino)propionamide

To 20.0 g of N-(tert-butoxycarbonyl)-L-alanine in 352 ml ofdichloromethane, 12.4 g of N,O-dimethylhydroxylamine hydrochloride, 15.7g of 1-hydroxybenzotriazole monohydrate, 24.3 g of1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 42.7 gof triethylamine were added, and the mixture was stirred at roomtemperature for 1.5 hours. After completion of the reaction, thereaction mixture was washed with 500 ml of saturated aqueous sodiumhydrogen carbonate, 500 ml of 1N aqueous hydrochloric acid and 500 ml ofwater in this order, the resulting organic layer was dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was evaporated under reduced pressure. The resulting residuewas washed with 200 ml of hexane to obtain 13.1 g of the desired productas white crystals.

m.p.: 144.0 to 145.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ5.22 (bs, 1H), 4.68 (bs, 1H), 3.77 (s,3H), 3.21 (s, 3H), 1.44 (s, 9H), 1.31 (d, J=6.9 Hz, 3H).

Step 2: Preparation of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl]carbamate

To 11.0 g of 2-bromo-3,5-dichloropyridine in 5 ml of tetrahydrofuran,36.4 ml of a 1.3 M tetrahydrofuran solution of isopropylmagnesiumchloride-lithium chloride complex was added dropwise with stirring at−20° C., and after the addition, the mixture was stirred at the sametemperature for 15 minutes. Then, to the reaction mixture, 5.0 g of(S)—N-methoxy-N-methyl-2-(tert-butoxycarbonylamino)propionamide in 36 mlof tetrahydrofuran was added dropwise, and after the addition, themixture was stirred at the same temperature for another 2 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 30 ml ofsaturated aqueous ammonium chloride and 10 ml of water and extractedwith ethyl acetate (40 ml×2), the resulting organic layers werecombined, washed with water (40 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 10:0 to 3:7) to obtain 4.5 g of the desired product asa pale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 (d, J=2.1 Hz, 1H), 7.84 (d, J=2.1Hz, 1H), 5.50 (bs, 1H), 5.32 (bs, 1H), 1.46 (s, 9H), 1.36 (d, J=7.2 Hz,3H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(17.5)−20.20° (CHCl₃, c=0.10)

Step 3: Preparation of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-hydroxyimino-1-methylethyl]carbamate

To a solution of 1.0 g of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl]carbamate and239 mg of hydroxylamine hydrochloride in 5 ml of ethanol, 272 mg ofpyridine was added, and the mixture was stirred at room temperature for18 hours. After completion of the reaction, the solvent was evaporatedunder reduced pressure, the resulting residue was mixed with 10 ml ofwater and extracted with ethyl acetate (10 ml×2), the resulting organiclayers were combined, dried over saturated aqueous sodium chloride andthen anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 40:60) as the eluent to obtain 740 mg of the desiredproduct as pale yellow crystals.

m.p.: 51.0 to 53.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.53 (d, J=2.1 Hz, 1H), 7.78 (d, J=2.1Hz, 1H), 5.15 (bs, 1H), 4.81 (bs, 1H), 1.3-1.65 (m, 12H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(17.8)−27.40° (CHCl₃, c=0.10)

Step 4: Preparation of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)-1-methylethyl]carbamate

To 655 mg of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-hydroxyimino-1-methylethyl]carbamatein 1.6 ml of N,N-dimethylformamide, 445 mg of potassium carbonate and789 mg of 2-iodopropane were added, and the mixture was stirred at roomtemperature for 18 hours. After completion of the reaction, the reactionmixture was mixed with 5 ml of water and extracted with ethyl acetate(10 ml×2), the resulting organic layers were combined, washed with water(10 ml×2) and dried over saturated aqueous sodium chloride and thenaqueous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 0:10to 3:7) as the eluent to obtain 411 mg of the desired product as acolorless oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 and 8.44 (d, J=2.1 Hz, 1H), 7.77and 7.73 (d, J=2.1 Hz, 1H), 5.20 (bs, 1H), 4.74 (bs, 1H), 4.25-4.5 (m,1H), 1.1-1.6 (m, 18H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(18.0)−29.90° (CHCl₃, c=0.14)

Step 5: Preparation of(S)-2-amino-1-(3,5-dichloropyridin-2-yl)propanone-β-isopropyloximehydrochloride

To 350 mg of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)-1-methylethyl]carbamatein 3 ml of 1,4-dioxane, 5 ml of a 1,4-dioxane solution (4 mol/L) ofhydrogen chloride was added, and the mixture was stirred at roomtemperature for 6 hours. After completion of the reaction, the solventwas evaporated under reduced pressure, and the resulting residue waswashed with 20 ml of hexane to obtain 253 mg of the desired product aswhite crystals.

m.p.: 215.0 to 216.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ9.00 (bs, 3H), 8.51 (d, J=2.1 Hz, 1H),7.76 (d, J=2.1 Hz, 1H), 4.35-4.6 (m, 2H), 1.73 and 1.57 (d, J=6.9 Hz,3H), 1.15-1.4 (m, 6H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ¹⁸⁶−15.50° (CHCl₃, c=0.10)

Step 6: Preparation of(S)—N-(2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)-1-methylethyl]-2-(trifluoromethyl)benzamide(compound No. 2-130 of the present invention)

To 210 mg of(S)-2-amino-1-(3,5-dichloropyridin-2-yl)propanone-O-isopropyloximehydrochloride in 1.3 ml of water, 151 mg of 2-(trifluoromethyl)benzoylchloride in 1.3 ml of dichloromethane and 278 mg of potassium carbonatewere added with stirring at room temperature, and the mixture wasstirred at the same temperature for 2 hours. After completion of thereaction, the resulting organic layer was collected and dried overanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 221 mg of the desired product as acolorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.48 and 8.40 (d, J=1.8 Hz, 1H),7.4-7.85 (m, 5H), 7.00 and 6.85 (bs, 1H), 5.7-5.85 and 5.15-5.3 (m, 1H),4.25-4.55 (m, 1H), 1.15-1.6 (m, 9H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(19.0)−13.20° (EtOH, c=0.10)

Step 7: Preparation of(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-[(Z)-isopropoxyimino]-1-methylethyl]-2-(trifluoromethyl)benzamide

240 mg of(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)-1-methylethyl]-2-(trifluoromethyl)benzamidewas dissolved in 4 ml of acetonitrile, and the solution was irradiatedwith light for 8 hours in a quartz cell (manufactured by Fine, 4 clearwindows for spectroscopy) using a 100 W high-pressure mercury lamp(manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B).After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 5:5) as the eluent to obtain 153 mg of the desired productas a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.48 (d, J=2.1 Hz, 1H), 7.78 (d, J=2.1Hz, 1H), 7.45-7.75 (m, 4H), 6.84 (bs, 1H), 5.15-5.3 (m, 1H), 4.25-4.45(m, 1H), 1.44 (d, J=6.6 Hz, 3H), 1.18 (d, J=6.0 Hz, 6H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(21.8)−8.60° (EtOH, c=0.10)

Synthetic Example 14

(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-[(Z)-ethoxyimino]-1-methylethyl]-2-(trifluoromethyl)benzamide(compound No. 2-124 of the present invention)

Step 1: Preparation of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-ethoxyimino-1-methylethyl]carbamate

To a solution of 1.0 g of the tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl]carbamateprepared in Step 2 in Synthetic Example 13 and 336 mg of ethoxyaminehydrochloride in 6.3 ml of ethanol, 272 mg of pyridine was added, andthe mixture was stirred at room temperature for 18 hours. Aftercompletion of the reaction, the solvent was distilled off under reducedpressure, the resulting residue was mixed with 10 ml of water andextracted with ethyl acetate (10 ml×2), the resulting organic layerswere combined, dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 40:60) as the eluent to obtain 824 mg of the desired produced as apale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.74 (d, J=2.1Hz, 1H), 5.19 (bs, 1H), 4.75 (bs, 1H), 4.26 and 4.11 (q, J=7.2 Hz, 2H),1.1-1.55 (m, 15H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(17.9)−30.00° (CHCl₃, c=0.10)

Step 2: Preparation of(S)-2-amino-1-(3,5-dichloropyridin-2-yl)propanone-O-ethyloximehydrochloride

To 780 mg of tert-butyl(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-ethoxyimino-1-methylethyl]carbamatein 3 ml of 1,4-dioxane, 5 ml of a 1,4-dioxane solution (4 mol/L) ofhydrogen chloride was added, and the mixture was stirred at roomtemperature for 6 hours. After completion of the reaction, the solventwas evaporated under reduced pressure, and the resulting residue waswashed with 20 ml of hexane to obtain 643 mg of the desired product asbeige crystals.

m.p.: 209.0 to 210.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.98 (bs, 3H), 8.52 (d, J=2.1 Hz, 1H),7.77 (d, J=2.1 Hz, 1H), 4.51 (bs, 1H), 4.35 and 4.20 (q, J=7.2 Hz, 2H),1.73 and 1.59 (d, J=7.2 Hz, 3H), 1.38 and 1.25 (t, J=7.2 Hz, 3H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(18.5)−10.90° (CHCl₃, c=0.10)

Step 3: Preparation of(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-ethoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamide(compound No. 2-122 of the present invention)

To 550 mg of(S)-2-amino-1-(3,5-dichloropyridin-2-yl)propanone-O-ethyloximehydrochloride in 3.7 ml of water, 423 mg of 2-(trifluoromethyl)benzoylchloride in 3.7 ml of dichloromethane and 763 mg of potassium carbonatewere added with stirring at room temperature, and the mixture wasstirred at the same temperature for 2 hours. After completion of thereaction, the organic layer was collected and dried over anhydroussodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 5:95 to 50:50) asthe eluent to obtain 800 mg of the desired product as a colorlessresinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 (d, J=2.1 Hz, 1H), 7.4-7.85 (m,5H), 6.98 and 6.81 (bs, 1H), 5.75-5.85 and 5.15-5.35 (m, 1H), 4.29 and4.12 (q, J=7.2 Hz, 2H), 1.15-1.65 (m, 6H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(19.0)−13.10° (EtOH, c=0.10)

Step 4: Preparation of(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-[(Z)-ethoxyimino]-1-methylethyl]-2-(trifluoromethyl)benzamide

580 mg of(S)—N-[2-(3,5-dichloropyridin-2-yl)-2-ethoxyimino-1-methylethyl]-2-(trifluoromethyl)benzamidewas dissolved in 3 ml of acetonitrile, and the solution was irradiatedwith light for 8 hours in a quartz cell (manufactured by Fine, 4 clearwindows for spectroscopy) using a 100 W high-pressure mercury lamp(manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B).After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 5:5) as the eluent to obtain 557 mg of the desired productas a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 (d, J=2.1 Hz, 1H), 7.4-7.85 (m,5H), 6.81 (bs, 1H), 5.15-5.35 (m, 1H), 4.12 (q, J=7.2 Hz, 2H), 1.45 (d,J=6.9 Hz, 3H), 1.20 (t, J=7.2 Hz, 3H).

Optical purity: 95% e.e.

Optical rotation: [α]_(D) ^(21.7)−11.40° (EtOH, c=0.10)

Synthetic Example 15(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(sec-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide(compound No. 2-136 of the present invention) Step 1: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide

To 5.0 g of the tert-butylN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]carbamate prepared in Step 1in Synthetic Example 12 in 2 ml of 1,4-dioxane, 25 ml of a 1,4-dioxanesolution (4 mol/L) of hydrogen chloride was added, and the mixture wasstirred at room temperature for 1.5 hours. After completion of thereaction, the solvent was evaporated under reduced pressure, theresulting residue was dissolved in 33 ml of water and 33 ml ofdichloromethane, and to the resulting solution, 4.5 g of potassiumcarbonate was added and further, 3.8 g of 2-(trifluoromethyl)benzoylchloride was added with stirring under cooling with ice, and the mixturewas stirred at room temperature for 2 hours. After completion of thereaction, the resulting organic layer was collected and dried overanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 2.8 g of the desired product as paleyellow crystals.

m.p.: 123.0 to 125.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.56 (d, J=2.1 Hz, 1H), 7.88 (d, J=2.1Hz, 1H), 7.5-7.8 (m, 4H), 6.69 (bs, 1H), 5.10 (d, J=5.1 Hz, 2H).

Step 2: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 2.8 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamidein 19 ml of ethanol, 1.0 g of hydroxylamine hydrochloride was added, andthe mixture was stirred at room temperature for 96 hours. Aftercompletion of the reaction, the solvent was evaporated under reducedpressure, the resulting residue was mixed with 50 ml of water andextracted with ethyl acetate (50 ml×2), the resulting organic layerswere combined, dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 2.8 g of the desired product as paleyellow crystals.

m.p.: 134.0 to 136.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.45 (d, J=2.4 Hz, 1H), 7.81and 7.80 (d, J=2.4 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 (bs, 1H), 4.80 and4.55 (d, J=6.3 Hz, 2H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(sec-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-009 of the present invention)

To a suspension of 500 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 352 mg of potassium carbonate in 1.3 ml of N,N-dimethylformamide,704 mg of 2-iodobutane was added, and the mixture was stirred at roomtemperature for 12 hours. After completion the reaction, the reactionmixture was mixed with 3 ml of water and extracted with ethyl acetate (3ml×2), the resulting organic layers were combined, washed with water (3ml×1) and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 522 mg of the desired product as apale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.44 (d, J=2.1 Hz, 1H), 7.81and 7.78 (d, J=2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 (bs, 1H), 4.76 and4.52 (d, J=5.7 Hz, 2H), 4.25-4.35 and 4.1-4.2 (m, 1H), 1.35-1.85 (m,2H), 1.30 and 1.17 (d, J=6.3 Hz, 3H), 0.94 and 0.83 (t, J=7.2 Hz, 3H).

Step 4: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(sec-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 522 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(sec-butoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 3 ml of acetonitrile, 1 mg of benzophenone was added, and the mixturewas irradiated with light for 12 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 50:50) as the eluent to obtain 416 mg of the desiredproduct as white crystals.

m.p.: 68.0 to 70.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.1 Hz, 1H), 7.45-7.8 (m,5H), 6.53 (bs, 1H), 4.53 (d, J=4.8 Hz, 2H), 4.05-4.2 (m, 1H), 1.35-1.7(m, 2H), 1.18 (d, J=6.3 Hz, 3H), 0.84 (t, J=7.5 Hz, 3H).

Synthetic Example 16(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

(Compound No. 2-114 of the present invention)

Step 1: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-002 of the present invention)

To a solution of 200 mg of theN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamideprepared in Step 1 in Synthetic Example 15 and 133 mg of methoxyaminehydrochloride in 2.7 ml of ethanol, 168 mg of pyridine was added, andthe mixture was stirred at 80° C. for 6 hours. After completion of thereaction, the reaction mixture was mixed with 10 ml of water andextracted with ethyl acetate (10 ml×1), the resulting organic layer waswashed with water (10 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 191 mg of thedesired product as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.45 (d, J=2.1 Hz, 1H), 7.80and 7.78 (d, J=2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.48 and 6.43 (bs, 1H),4.73 and 4.53 (d, J=6.3 Hz, 2H), 4.06 and 4.02 (s, 3H).

Step 2: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

191 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamidein 4 ml of acetonitrile was irradiated with light for 11 hours in aquartz cell (manufactured by Fine, 4 clear windows for spectroscopy)using a 100 W high-pressure mercury lamp (manufactured by USHIO INC.,lamp: UM-102, power supply: UM-103B-B). After completion of thereaction, the solvent was evaporated under reduced pressure, and theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluentto obtain 149 mg of the desired product as white crystals.

m.p.: 88.0 to 89.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 (d, J=2.0 Hz, 1H), 7.78 (d, J=2.0Hz, 1H), 7.35-7.75 (m, 4H), 6.45 (bs, 1H), 4.53 (d, J=4.8 Hz, 2H), 4.02(s, 3H).

Synthetic Example 17(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-[1-(4-fluorophenyl)ethoxyimino]ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-174 of the present invention) Step 1: Preparation ofN-[2-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamide

To 45.2 g of 2-[2-(trifluoromethyl)benzoylamino]acetic acid in 609 ml ofdichloromethane, 21.4 g of N,O-dimethylhydroxylamine hydrochloride, 42.0g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 73.8 gof triethylamine and 2.2 g of 4-(dimethylamino)pyridine were added, andthe mixture was stirred at room temperature for 18 hours. Aftercompletion of the reaction, the reaction mixture was washed with 500 mlof saturated anhydrous sodium hydrogen carbonate, 500 ml of 1N aqueoushydrochloric acid twice and 500 ml of water in this order, the resultingorganic layer was dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was washed with 200 ml of hexane toobtain 31.4 g of the desired product as white crystals.

m.p.: 106.0 to 107.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ7.5-7.75 (m, 4H), 6.70 (bs, 1H), 4.40(d, J=3.9 Hz, 2H), 3.77 (s, 3H), 3.25 (s, 3H).

Step 2: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide

To 17.6 g of 2-bromo-3,5-dichloropyridin in 5 ml of tetrahydrofuran,58.3 ml of a 1.3M tetrahydrofuran solution of isopropylmagnesiumchloride-lithium chloride complex was added dropwise with stirring at−20° C., and after the addition, the mixture was stirred at the sametemperature for 30 minutes. Then, to the reaction mixture, 10.0 g ofN42-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamide in57.4 ml of tetrahydrofuran was added dropwise, and after the addition,the mixture was stirred at room temperature for another 3 hours. Aftercompletion of the reaction, the reaction mixture was mixed with 100 mlof saturated aqueous ammonium chloride and 100 ml of water and extractedwith ethyl acetate (150 ml×2), the resulting organic layers werecombined, washed with water (100 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasdistilled off under reduced pressure. The residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 50:50) as the eluent to obtain 3.0 g of the desired productas pale yellow crystals.

m.p.: 123.0 to 125.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.56 (d, J=2.1 Hz, 1H), 7.88 (d, J=2.1Hz, 1H), 7.5-7.8 (m, 4H), 6.69 (bs, 1H), 5.10 (d, J=5.1 Hz, 2H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 2.8 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamidein 19 ml of ethanol, 1.0 g of hydroxylamine hydrochloride was added, andthe mixture was stirred at room temperature for 96 hours. Aftercompletion of the reaction, the solvent was evaporated under reducedpressure, the resulting residue was mixed with 50 ml of water andextracted with ethyl acetate (50 ml×2), the resulting organic layerswere combined, dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 2.8 g of the desired product as whitecrystals.

m.p.: 134.0 to 136.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.45 (d, J=2.4 Hz, 1H), 7.81and 7.80 (d, J=2.4 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 (bs, 1H), 4.80 and4.55 (d, J=6.3 Hz, 2H).

Step. 4: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-[1-(4-fluorophenyl)ethoxyimino]ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-173 of the present invention)

To a suspension of 200 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 211 mg of potassium carbonate in 2 ml of N,N-dimethylformamide, 155mg of 1-(1-bromoethyl)-4-fluorobenzene was added, and the mixture wasstirred at room temperature for 18 hours. After completion of thereaction, the reaction mixture was mixed with 3 ml of water andextracted with ethyl acetate (3 ml×2), the resulting organic layers werecombined, washed with water (3 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 5:95 to 50:50) as the eluent to obtain 171 mg of thedesired product as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.42 (d, J=2.1 Hz, 1H), 7.80and 7.77 (d, J=2.1 Hz, 1H), 6.0-7.75 (m, 8H), 6.40 (bs, 1H), 5.38 and5.21 (q, J=6.9 Hz, 1H), 4.81 and 4.49 (d, J=5.7 Hz, 2H), 1.64 and 1.45(d, J=6.9 Hz, 3H).

Step 5: Preparation of(Z)—N-[2-(3,5-dichloropyridin-2-yl)-2-[1-(4-fluorophenyl)ethoxyimino]ethyl]-2-(trifluoromethyl)benzamide

To 171 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-[1-(4-fluorophenyl)ethoxyimino]ethyl]-2-(trifluoromethyl)benzamidein 3 ml of acetonitrile, 1 mg of benzophenone was added, and the mixturewas irradiated with light for 12 hours in a quartz cell (manufactured byFine, 4 clear windows for spectroscopy) using a 100 W high-pressuremercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply:UM-103B-B). After completion of the reaction, the solvent was evaporatedunder reduced pressure, and the resulting residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 50:50) as the eluent to obtain 98 mg of the desired productas a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 (d, J=2.0 Hz, 1H), 7.80 (d, J=2.0Hz, 1H), 6.85-7.75 (m, 8H), 6.38 (bs, 1H), 5.22 (q, J=6.6 Hz, 1H), 4.50(d, J=5.5 Hz, 2H), 1.45 (d, J=6.6 Hz, 3H).

Synthetic Example 18(Z)—N-[2-(3,5-dibromopyridine-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-236 of the Present Invention) Step 1: Preparation ofN-[2-(3,5-dibromopyridine-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide

To 5.5 g of 3,5-dibromopyridine in 1 ml of tetrahydrofuran, 22.7 ml of a1.0M tetrahydrofuran-toluene solution of2,2,6,6-tetramethylpiperidinylmagnesium chloride-lithium chloridecomplex was added dropwise with stirring at −20° C., and after theaddition, the mixture was stirred at the same temperature for 30minutes. Then, to the reaction mixture, 3.0 g of theN-[2-methoxy(methyl)amino-2-oxoethyl]-2-(trifluoromethyl)benzamideprepared in Step 1 in Synthetic Example 17 in 17 ml of tetrahydrofuranwas added dropwise, and after the addition, the mixture was stirred atthe same temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 30 ml of saturated aqueousammonium chloride and 20 ml of water and extracted with ethyl acetate(50 ml×2), the resulting organic layers were combined, washed with water(50 ml×1) and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 659 mg of the desired product as apale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.69 (d, J=2.1 Hz, 1H), 8.25 (d, J=2.1Hz, 1H), 7.1-7.8 (m, 4H), 6.68 (bs, 1H), 5.10 (d, J=4.8 Hz, 2H).

Step 2: Preparation ofN-[2-(3,5-dibromopyridine-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-235 of the present invention)

To 200 mg ofN-[2-(3,5-dibromopyridine-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamidein 1.4 ml of ethanol, 63 mg of ethoxyamine hydrochloride was added, andthe mixture was stirred at room temperature for 18 hours. Aftercompletion of the reaction, the solvent was evaporated under reducedpressure, the resulting residue was mixed with 4 ml of water andextracted with ethyl acetate (4 ml×2), the resulting organic layers werecombined, dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 5:95 to 50:50) asthe eluent to obtain 195 mg of the desired product as a pale yellowresinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.63 and 8.58 (d, J=2.1 Hz, 1H), 8.14and 8.10 (d, J=2.1 Hz, 1H), 7.1-7.75 (m, 4H), 6.43 (bs, 1H), 4.75 and4.53 (d, J=5.7 Hz, 2H), 4.30 and 4.13 (q, J=7.2 Hz, 2H), 1.36 and 1.22(t, J=7.2 Hz, 3H).

Step 3: Preparation of(Z)—N-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

195 mg ofN-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamidewas dissolved in 3 ml of acetonitrile, and the solution was irradiatedwith light for 12 hours in a quartz cell (manufactured by Fine, 4 clearwindows for spectroscopy) using a 100 W high-pressure mercury lamp(manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B).After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 5:5) as the eluent to obtain 125 mg of the desired productas a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.63 (d, J=2.1 Hz, 1H), 8.10 (d, J=2.1Hz, 1H), 7.1-7.75 (m, 4H), 6.52 (bs, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.13(q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H).

Synthetic Example 19N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-005 of the Present Invention) Step 1: Preparation of3,5-dichloro-2-(nitromethyl)pyridine

To 30.74 g of potassium tert-butoxide in 100 ml of dimethylsulfoxide,16.72 g of nitromethane was added dropwise with stirring under coolingwith ice, and after the addition, the mixture was stirred at roomtemperature for another 1 hour. Then, the reaction mixture was cooledwith ice again, and to the reaction mixture, 25.00 g of2,3,5-trichloropyridine in 100 ml of dimethylsulfoxide was addeddropwise with stirring, and after the addition, the mixture was stirredat 70° C. for another 6 hours. After completion of the reaction, thereaction mixture was allowed to cool to room temperature, poured into200 ml of 10% aqueous hydrochloric acid with stirring under cooling withice and extracted with ethyl acetate (200 ml×1). The resulting organiclayer was washed with water (100 ml×1) and dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 5:95 to 10:90) as the eluent to obtain 10.10 g of thedesired product as a pale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.53 (d, J=2.4 Hz, 1H), 7.84 (d, J=2.4Hz, 1H), 5.76 (s, 2H).

Step 2: Preparation of N-chloromethyl-2-(trifluoromethyl)benzamide

To 15.50 g of N-hydroxymethyl-2-(trifluoromethyl)benzamide in 200 ml ofdichloromethane, 16.83 g of thionyl chloride was added dropwise withstirring under cooling with ice, and after the addition, the mixture wasstirred at room temperature for another 3 hours. After completion of thereaction, the solvent was evaporated under reduced pressure, and theprecipitated solid was washed with 50 ml of hexane to obtain 16.90 g ofthe desired product as white crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ7.5-7.75 (m, 4H), 6.40 (bs, 1H), 5.32(d, J=7.5 Hz, 2H).

Step 3: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide

To 6.57 g of potassium tert-butoxide in 100 ml of N,N-dimethylformamide,10.10 g of 3,5-dichloro-2-(nitromethyl)pyridine was added dropwise withstirring under cooling with ice, and after the addition, the mixture wasstirred at the same temperature for another 30 minutes. Then, to thereaction mixture, 11.59 g of N-chloromethyl-2-(trifluoromethyl)benzamidein 50 ml of N,N-dimethylformamide was added dropwise with stirring undercooing with ice, and after the addition, the mixture was stirred at roomtemperature for another 2 hours. After completion of the reaction, thereaction mixture was carefully poured into 100 ml of ice-water,acidified with 10% aqueous hydrochloric acid and extracted with ethylacetate (100 ml×2). The resulting organic layers were combined, washedwith water (100 ml×1) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 14.00 g of the desired productas a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.48 (d, J=2.1 Hz, 1H), 7.87 (d, J=2.1Hz, 1H), 7.45-7.75 (m, 4H), 6.49 (bs, 1H), 6.35 (dd, J=7.2, 4.5 Hz, 1H),4.3-4.5 (m, 2H).

Step 4: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 14.00 g ofN-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamidein 70 ml of a mixture of N,N-dimethylformamide-water (7:1), 16.62 g ofsodium nitrite was added, and the mixture was stirred at 60° C. for 18hours. After completion of the reaction, the reaction mixture wasallowed to cool to room temperature, poured into 100 ml of water andextracted with ethyl acetate (100 ml×2). The resulting organic layerswere combined, washed with water (50 ml×1) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waspurified by silica gel column chromatography using ethyl acetate-hexane(with a gradient of from 3:7 to 1:1) as the eluent to obtain 5.90 g ofthe desired product as pale yellow crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.52 and 8.45 (d, J=2.4 Hz, 1H), 7.81and 7.80 (d, J=2.4 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 (bs, 1H), 4.80 and4.55 (d, J=6.3 Hz, 2H).

Step 5: Preparation ofN-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a suspension of 450 mg ofN-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 476 mg of potassium carbonate in 5 ml of N,N-dimethylformamide, 313mg of 2-iodopropane was added, and the mixture was stirred at roomtemperature for 12 hours. After completion of the reaction, the reactionmixture was mixed with 20 ml of water and extracted with ethyl acetate(25 ml×2), the resulting organic layers were combined, washed with water(20 ml×1) and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 1:9to 3:7) as the eluent to obtain 121 mg of a colorless resinoussubstance. The resinous substance was dissolved in 10 ml of ethanol, thesolution was mixed with 1 ml of a 1,4-dioxane solution (4 mol/L) ofhydrogen chloride and stirred at 70° C. for 5 hours, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 99 mg of thedesired product as a colorless resinous substance (E/Z=50/50).

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.50 and 8.45 (d, J=2.1 Hz, 1H), 7.81and 7.78 (d, J=2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 and 6.49 (bs, 1H),4.76 and 4.53 (d, J=6.0 Hz, 2H), 4.45-4.55 and 4.3-4.45 (m, 1H), 1.33and 1.18 (d, J=6.3 Hz, 6H).

Synthetic Example 20(Z)—N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-216 of the present invention) Step 1: Preparation of5-bromo-3-chloro-2-(nitromethyl)pyridine

To 12.4 g of potassium tert-butoxide in 79 ml of dimethylsulfoxide, 6.7g of nitromethane was added dropwise with stirring under cooling withice, and after the addition, the mixture was stirred at room temperaturefor another 1 hour. Then, the reaction mixture was added dropwise to25.0 g of 5-bromo-2,3-dichloropyridine in 20 ml of dimethylsulfoxidewith stirring under cooling with ice, and after the addition, themixture was stirred at room temperature for 23 hours and at 50° C. for 6hours. After completion of the reaction, the reaction mixture wasallowed to cool to room temperature, mixed with 100 ml of water and 100ml of saturated aqueous ammonium chloride and extracted with ethylacetate (200 ml×2). The resulting organic layers were combined, washedwith water (100 ml×3) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 5:95 to 30:70) as the eluent to obtain 7.8 g of the desired productas a pale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.62 (d, J=2.1 Hz, 1H), 7.98 (d, J=2.1Hz, 1H), 5.74 (s, 2H).

Step 2: Preparation ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide

To 4.2 g of potassium tert-butoxide in 72 ml of N,N-dimethylformamide,7.8 g of 5-bromo-3-chloro-2-(nitromethyl)pyridine was added dropwisewith stirring under cooling with ice, and after the addition, themixture was stirred at the same temperature for another 1 hour. Then, tothe reaction mixture, 4.7 g of theN-chloromethyl-2-(trifluoromethyl)benzamide prepared in Step 2 inSynthetic Example 19 in 30 ml of N,N-dimethylformamide was addeddropwise with stirring under cooling with ice, and after the addition,the mixture was stirred at room temperature for another 2 hours. Aftercompletion of the reaction, the reaction mixture was carefully pouredinto 100 ml of ice-water, acidified with 10% aqueous hydrochloric acidand extracted with ethyl acetate (100 ml×2). The resulting organiclayers were combined, washed with water (100 ml×2) and dried oversaturated aqueous sodium chloride and then anhydrous sodium sulfate, andthe solvent was distilled off under reduced pressure. The resultingresidue was purified by silica gel column chromatography using ethylacetate-hexane (with a gradient of from 5:95 to 50:50) as the eluent toobtain 6.0 g of the desired product as a pale yellow oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.57 (d, J=1.8 Hz, 1H), 8.01 (d, J=1.8Hz, 1H), 7.4-7.75 (m, 4H), 6.48 (bs, 1H), 6.25-6.4 (m, 1H), 4.25-4.5 (m,2H).

Step 3: Preparation ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 6.0 g ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamidein 65 ml of a mixture of N,N-dimethylformamide-water (7:1), 6.4 g ofsodium nitrite was added, and the mixture was stirred at 60° C. for 18hours. After completion of the reaction, the reaction mixture wasallowed to cool to room temperature, poured into 100 ml of water, mixedwith 20 ml of saturated aqueous ammonium chloride and extracted withethyl acetate (100 ml×2). The resulting organic layers were combined,washed with water (50 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 2:8 to 6:4) as the eluent to obtain 3.1 g of thedesired product as a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.6-8.65 and 8.5-8.6 (m, 1H), 7.9-8.0(m, 1H), 7.35-7.75 (m, 4H), 6.51 (bs, 1H), 4.75-4.85 and 4.5-4.6 (m,2H).

Step 4: Preparation ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a suspension of 200 mg ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 189 mg of potassium carbonate in 1 ml of N,N-dimethylformamide, 97mg of iodomethane was added, and the mixture was stirred at roomtemperature for 23 hours. After completion of the reaction, the reactionmixture was mixed with 10 ml of water and extracted with ethyl acetate(20 ml×2), the resulting organic layers were combined, washed with water(10 ml×2) and dried over saturated aqueous sodium chloride and thenanhydrous sodium sulfate, and the solvent was evaporated under reducedpressure. The resulting residue was purified by silica gel columnchromatography using ethyl acetate-hexane (with a gradient of from 5:95to 50:50) as the eluent to obtain 143 mg of the desired product as apale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.61 and 8.56 (d, J=1.8 Hz, 1H), 7.96and 7.94 (d, J=1.8 Hz, 1H), 7.35-7.75 (m, 4H), 6.48 (bs, 1H), 4.74 and4.54 (d, J=5.4 Hz, 2H), 4.07 and 3.88 (s, 3H).

Step 5: Preparation of(Z)—N12-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

143 mg ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamidewas dissolved in 3 ml of acetonitrile, and the solution was irradiatedwith light for 12 hours in a quartz cell (manufactured by Fine, 4 clearwindows for spectroscopy) using a 100 W high-pressure mercury lamp(manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B).After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was washed with 10 ml ofhexane to obtain 63 mg of the desired product as pale yellow crystals.

m.p.: 85.0 to 86.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.61 (d, J=1.8 Hz, 1H), 7.94 (d, J=1.8Hz, 1H), 7.5-7.75 (m, 4H), 6.48 (bs, 1H), 4.54 (d, J=5.4 Hz, 2H), 3.88(s, 3H).

Synthetic Example 21(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-020 of the present invention) Step 1: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-nitroethyl]-2-(trifluoromethyl)benzamide

To 10.26 g of potassium tert-butoxide in 80 ml of N,N-dimethylformamide,20.00 g of 3-chloro-2-nitromethyl-5-(trifluoromethyl)pyridine was addeddropwise with stirring under cooling with ice, and after the addition,the mixture was stirred at the same temperature for another 30 minutes.Then, to the reaction mixture, 18.77 g of theN-chloromethyl-2-(trifluoromethyl)benzamide prepared in Step 2 inSynthetic Example 19 in 20 ml of N,N-dimethylformamide was addeddropwise with stirring under cooling with ice, and after the addition,the mixture was stirred at room temperature for another 3 hours. Aftercompletion of the reaction, the reaction mixture was carefully pouredinto 150 ml of 5% aqueous hydrochloric acid under cooling with ice andextracted with ethyl acetate (100 ml×2). The resulting organic layerswere combined, washed with water (100 ml×2) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The precipitated solidwas purified with 30 ml of diisopropyl ether to obtain 19.80 g of thedesired product as white crystals.

m.p.: 100.0 to 102.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.78 (s, 1H), 8.09 (s, 1H), 7.45-7.75(m, 4H), 6.50 (bs, 1H), 6.4-6.5 (m, 1H), 4.35-4.5 (m, 2H).

Step 2: Preparation ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

To 19.80 g ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-nitroethyl]-2-(trifluoromethyl)benzamidein 100 ml of a mixture of N,N-dimethylformamide-water (7:1), 21.65 g ofsodium nitrite was added, and the mixture was stirred at from 45 to 50°C. for 12 hours. After completion of the reaction, the reaction mixturewas allowed to cool to room temperature, poured into 150 ml of water andextracted with ethyl acetate (100 ml×2). The resulting organic layerswere combined, washed with water (100 ml×1) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waspurified by silica gel column chromatography using ethyl acetate-hexane(with a gradient of from 3:7 to 1:1) as the eluent to obtain 11.10 g ofthe desired product as white crystals.

m.p.: 110.0 to 113.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.82 and 8.75 (s, 1H), 8.04 (s, 1H),7.35-7.7 (m, 4H), 6.52 (bs, 1H), 4.83 and 4.59 (d, J=6.3 Hz, 2H).

Step 3: Preparation of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-019 of the present invention)

To a suspension of 20.00 g ofN-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideand 19.48 g of potassium carbonate in 105 ml of N,N-dimethylformamide,10.38 g of 2-iodopropane was added, and the mixture was stirred at roomtemperature for 12 hours. After completion of the reaction, the reactionmixture was mixed with 200 ml of water and extracted with ethyl acetate(100 ml×3), the resulting organic layers were combined, washed withwater (100 ml×1) and dried over saturated aqueous sodium chloride andthen anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 11.00 g of the desired productas white crystals.

m.p.: 81.0 to 83.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.73 (s, 1H), 8.01 (s, 1H), 7.35-7.75(m, 4H), 6.48 (bs, 1H), 4.78 (d, J=5.1 Hz, 2H), 4.45-4.6 (m, 1H), 1.34(d, J=6.0 Hz, 6H).

Step 4: Preparation of(Z)—N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

11.00 g of(E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamidewas dissolved in 30 ml of acetic acid and stirred at 70° C. for 1 hour.After completion of the reaction, the solvent was evaporated underreduced pressure, and the resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-chloroform (with a gradient offrom 0:100 to 5:95) as the eluent to obtain 5.63 g of the desiredproduct as white crystals.

m.p.: 97.0 to 98.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.79 (s, 1H), 7.99 (s, 1H), 7.5-7.75 (m,4H), 6.49 (bs, 1H), 4.56 (d, J=5.1 Hz, 2H), 4.3-4.45 (m, 1H), 1.19 (d,J=6.0 Hz, 6H).

Synthetic Example 22N-[2-[3-chloro-5-(3,3-dimethyl-1-butynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-248 of the present invention) Step 1: Preparation ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-181 of the present invention)

To a suspension of 1.80 g of theN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamideprepared in Step 3 in Synthetic Example 20 and 0.86 g of potassiumcarbonate in 10 ml of N,N-dimethylformamide, 1.30 g of 2-iodopropane wasadded, and the mixture was stirred at room temperature for 13 hours.After completion of the reaction, the reaction mixture was mixed with100 ml of water and extracted with ethyl acetate (50 ml×2), theresulting organic layers were combined, washed with water (100 ml×1) anddried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 1:4 to 2:2) as the eluentto obtain 1.26 g of the desired product as a pale yellow resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.60 and 8.54 (d, J=1.9 Hz, 1H), 7.96and 7.93 (d, J=1.9 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 and 6.49 (bs, 1H),4.75 and 4.53 (d, J=6.1 and 5.0 Hz, 2H), 4.51 and 4.37 (sep, J=6.3 Hz,1H), 1.33 and 1.19 (d, J=6.3 Hz, 6H).

Step 2: Preparation ofN-[2-[3-chloro-5-(3,3-dimethyl-1-butynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a solution of 0.15 g ofN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamideand 0.05 g of 3,3-dimethyl-1-butyne in 3 ml of triethylamine, 0.04 g ofcopper(I) iodide and 0.02 g of dichlorobistriphenylphosphinepalladium(II) were added, and the mixture was stirred at 80° C. for 3hours. After completion of the reaction, the reaction mixture wasallowed to cool to room temperature, mixed with 10 ml of water andextracted with ethyl acetate (20 ml×1). The resulting organic layer waswashed with water (10 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 1:5 to 2:4) as the eluent to obtain 0.15 g of the desired productas a yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.49 and 8.43 (d, J=1.7 Hz, 1H), 7.76and 7.73 (d, J=1.7 Hz, 1H), 7.45-7.8 (m, 4H), 6.60 (bs, 1H), 4.77 and4.52 (d, J=5.8 and 4.8 Hz, 2H), 4.50 and 4.35 (sep, J=6.3 Hz, 1H), 1.32(s, 9H), 1.31 and 1.17 (d, J=6.3 Hz, 6H).

Synthetic Example 23N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzthioamide(Compound No. 5-001 of the present invention)

To 222 mg of theN-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamideprepared in Step 4 in Synthetic Example 20 in 5 ml of 1,4-dioxane, 200mg of Lawesson's Reagent(2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide)was added, and the mixture was stirred at 80° C. for 3 hours and then atroom temperature for 12 hours. After completion of the reaction, thereaction mixture was mixed with 40 ml of 0.05M aqueous sodium hydroxideand extracted with a mixture of ethyl acetate-diethyl ether (2:1) (30ml×1), the resulting organic layer was washed with 40 ml of 0.2M aqueoussodium hydroxide and dried over saturated aqueous sodium chloride andthen anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 2:8) as the eluent to obtain 133 mg of the desired productas a brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.61 and 8.53 (d, J=2.0 Hz, 1H), 8.33and 8.08 (bs, 1H), 7.98 and 7.96 (d, J=2.0 Hz, 1H), 7.35-7.7 (m, 4H),5.10 and 4.80 (d, J=5.1 and 4.4 Hz, 2H), 4.09 and 3.89 (s, 3H).

Synthetic Example 24N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-N-methyl-2-(trifluoromethyl)benzamide(Compound No. 4-005 of the present invention)

To 33 mg of 60% sodium hydride in oil in 5 ml of tetrahydrofuran, 300 mgof theN-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamideprepared in Step 1 in Synthetic Example 16 in 3 ml of tetrahydrofuranwas added dropwise with stirring and cooling with ice, and the mixturewas stirred at the same temperature for 30 minutes. Then, the reactionmixture was mixed with 157 mg of methyl iodide, warmed to roomtemperature and stirred for another 1 hour. After completion of thereaction, the reaction mixture was poured into 20 ml of ice-water andextracted with ethyl acetate (50 ml×1), the organic layer was washedwith water (20 ml×1) and dried over saturated aqueous sodium chlorideand then anhydrous sodium sulfate, and the solvent was evaporated underreduced pressure. The resulting residue was purified by silica gelcolumn chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 2:8) as the eluent to obtain 203 mg of the desired productas a pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.51 and 8.40 (d, J=2.0 Hz, 1H), 7.81and 7.80 (d, J=2.0 Hz, 1H), 7.4-7.75 (m, 3H), 6.9-7.15 (m, 1H), 5.00 and4.53 (d, J=15.0 Hz, 1H), 4.75 and 4.34 (d, J=15.0 Hz, 1H), 4.06 and 3.96(s, 3H), 3.02 and 2.82 (s, 3H).

Synthetic Example 25N-cyclopropyl-N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide(Compound No. 17-009 of the Present Invention) Step 1: Preparation of2-cyclopropylamino-1-(3,5-dichloropyridin-2-yl)ethanone-O-methyloxime

To 700 mg of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-methyloximeprepared in the same manner as in Steps 1 to 3 in Synthetic Example 2 in10 ml of acetonitrile, 402 mg of cyclopropylamine in 5 ml ofacetonitrile was added, and the mixture was stirred at room temperaturefor 18 hours. After completion of the reaction, the reaction mixture wasmixed with 30 ml of water and extracted with ethyl acetate (40 ml×2, theresulting organic layers were combined, washed with water (30 ml×1) anddried over saturated aqueous sodium chloride and then anhydrous sodiumsulfate, and the solvent was evaporated under reduced pressure. Theresulting residue was purified by silica gel column chromatography usingethyl acetate-hexane (with a gradient of from 3:7 to 5:5) as the eluentto obtain 450 mg of the desired product as a colorless resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.48 (bs, 1H), 7.78 (bs, 1H), 3.8-4.05(m, 5H), 1.95-2.1 (m, 1H), 0.15-0.4 (m, 4H).

Step 2: Preparation ofN-cyclopropyl-N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide

To 204 mg of5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid in 3ml of dichloromethane, 16 mg of N,N-dimethylformamide and 161 mg ofoxalyl chloride were added, and the mixture was stirred at roomtemperature for 1 hour. After completion of the reaction, the solventwas evaporated under reduced pressure, the resulting residue wasdissolved in 5 ml of dichloromethane, and added dropwise to a solutionof 220 mg of2-cyclopropylamino-1-(3,5-dichloropyridin-2-yl)ethanone-β-methyloximeand 162 mg of triethylamine in 10 ml of dichloromethane with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 20 ml of water andextracted with chloroform (20 ml×1), the resulting organic layer waswashed with water (20 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:4 to 2:3) as the eluent to obtain 252 mg of thedesired product as white crystals.

m.p.: 95.0 to 97.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.43 (d, J=2.1 Hz, 1H), 7.77 (d, J=2.1Hz, 1H), 4.81 (bs, 2H), 4.04 (s, 3H), 3.78 (s, 3H), 2.7-2.8 (m, 1H),0.55-0.7 (m, 4H).

Synthetic Example 26N-[2-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide(Compound No. 2-223 of the present invention) Step 1: Preparation of1-(3-chloro-5-hydroxypyridin-2-yl)ethanone

To a solution of 3.8 g of the 1-(3,5-dichloropyridin-2-yl)ethanoneprepared in Step 1 in Synthetic Example 2 and 13.8 g of potassiumcarbonate in 20 ml of dimethylsulfoxide, 5.9 g of acetaldoxime wasadded, and the mixture was stirred at 80° C. for 4 hours. Aftercompletion of the reaction, the reaction mixture was allowed to cool toroom temperature, mixed with 50 ml of water and washed with diethylether (30 ml×1), the resulting aqueous layer was acidified with 6Naqueous hydrochloric acid and extracted with ethyl acetate (25 ml×2).The resulting organic layers were combined, dried over saturated aqueoussodium chloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure to obtain 1.0 g of desired crudeproduct as brown crystals. The crystals were used in the next stepwithout further purification.

m.p.: 143.0 to 145.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.20 (d, J=2.4 Hz, 1H), 7.30 (d, J=2.4Hz, 1H), 2.68 (s, 3H).

Step 2: Preparation of1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone

To 1.0 g of 1-(3-chloro-5-hydroxypyridin-2-yl)ethanone in 15 ml ofN,N-dimethylformamide, 1.2 g of potassium carbonate and 1.6 g of2,2,2-trifluoroethyl trifluoromethanesulfonate were added, and themixture was stirred at room temperature for 12 hours. After completionof the reaction, the reaction mixture was mixed with 40 ml of water andextracted with ethyl acetate (50 ml×1), the resulting organic layer waswashed with water (20 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The residue was purified by silicagel column chromatography using ethyl acetate-hexane (with a gradient offrom 1:9 to 3:7) as the eluent to obtain 1.2 g of the desired product aswhite crystals.

m.p.: 52.0 to 55.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.30 (d, J=2.7 Hz, 1H), 7.33 (d, J=2.7Hz, 1H), 4.47 (q, J=7.8 Hz, 2H), 2.68 (s, 3H).

Step 3: Preparation of2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone

To 1.1 g of 1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanonein 20 ml of tetrahydrofuran, 1.6 g of triethylphenylammonium tribromidewas added, and the mixture was stirred at room temperature for 12 hours.After completion of the reaction, the precipitated solid was filteredoff through celite, and the solvent was evaporated under reducedpressure to obtain 1.3 g of the desired crude product as a pale yellowoil. The oil was used in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.32 (d, J=2.7 Hz, 1H), 7.37 (d, J=2.7Hz, 1H), 4.72 (s, 2H), 4.50 (q, J=7.8 Hz, 2H).

Step 4: Preparation of2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime

To 1.3 g of2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone in 10ml of ethanol, 362 mg of methoxyamine hydrochloride was added, and themixture was stirred at room temperature for 13 hours. After completionof the reaction, the solvent was evaporated under reduced pressure, andthe resulting residue was purified by silica gel column chromatographyusing ethyl acetate-hexane (with a gradient of from 0:100 to 5:95) toobtain 1.2 g of the desired product as a colorless oil.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.30 (d, J=2.4 Hz, 1H), 7.37 (d, J=2.4Hz, 1H), 4.51 (s, 2H), 4.44 (q, J=7.5 Hz, 2H), 4.10 (s, 3H).

Step 5: Preparation ofN-[2-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-2-(methoxyimino)ethyl]phthalimide

To 1.0 g of2-bromo-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-β-methyloximein 10 ml of N,N-dimethylformamide, 615 mg of potassium phthalimide wasadded, and the mixture was stirred at room temperature for 13 hours.After completion of the reaction, the reaction mixture was mixed with 30ml of water and extracted with ethyl acetate (20 ml×1), the resultingorganic layer was washed with water (20 ml×1) and dried over saturatedaqueous sodium chloride and then anhydrous sodium sulfate, and thesolvent was evaporated under reduced pressure. The resulting residue waswashed with 10 ml of diisopropyl ether to obtain 790 mg of the desiredproduct as pale orange crystals.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.08 (d, J=2.4 Hz, 1H), 7.55-7.9 (m,4H), 7.28 (d, J=2.4 Hz, 1H), 4.98 (s, 2H), 4.33 (q, J=7.8 Hz, 2H), 4.04(s, 3H).

Step 6: Preparation of2-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloxime

To 790 mg ofN-[2-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-2-(methoxyimino)ethyl]phthalimidein 10 ml of ethanol, 187 mg of hydrazine monohydrate was added andrefluxed with heating for 1 hour with stirring. After completion of thereaction, the reaction mixture was allowed to cool to room temperature,mixed with 30 ml of water and extracted with ethyl acetate (25 ml×2).The resulting organic layers were combined, washed with water (20 ml×1)and dried over saturated aqueous sodium chloride and then anhydroussodium sulfate, and the solvent was evaporated under reduced pressure toobtain 446 mg of the desired crude product as a brown oil. The oil wasused in the next step without further purification.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.32 and 8.31 (d, J=2.4 Hz, 1H), 7.38and 7.37 (d, J=2.4 Hz, 1H), 4.4-4.5 (m, 2H), 4.03 and 3.91 (s, 2H), 3.88and 3.75 (s, 3H).

Step 7: Preparation ofN-[2-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

To a solution of 227 mg of2-amino-1-[3-chloro-5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethanone-O-methyloximeand 92 mg of triethylamine in 5 ml of dichloromethane, 175 mg of2-(trifluoromethyl)benzoyl chloride was added dropwise with stirringunder cooling with ice, and after the addition, the mixture was stirredat room temperature for another 1 hour. After completion of thereaction, the reaction mixture was mixed with 10 ml of water andextracted with chloroform (10 ml×1), the resulting organic layer waswashed with water (10 ml×1) and dried over saturated aqueous sodiumchloride and then anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The resulting residue was purified bysilica gel column chromatography using ethyl acetate-hexane (with agradient of from 1:9 to 3:7) as the eluent to obtain 249 mg of thedesired product as a colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ8.31 and 8.27 (d, J=3.0 Hz, 1H),7.35-7.75 (m, 5H), 6.52 and 6.45 (bs, 1H), 4.75 and 4.53 (d, J=6.0 Hz,2H), 4.43 (q, J=7.8 Hz, 2H), 4.06 and 3.88 (s, 3H).

The compounds of the present invention can be produced in accordancewith the processes and Examples previously described. Examples of theoxime-substituted amide compounds of the present invention produced inthe same manners as in Synthetic Examples 1 to 26 are shown in Tables 4to 32, and examples of their intermediates are shown in Tables 33 to 45.However, the oxime-substituted amide compounds of the present inventionand their intermediates are by no means restricted thereto.

In the Tables, Et denotes ethyl group, n-Pr denotes normal propyl group,i-Pr and Pr-i denote isopropyl group, c-Pr and Pr-c denote cyclopropylgroup, n-Bu denotes normal butyl group, i-Bu denotes isobutyl group,s-Bu denotes sec-butyl group, c-Bu and Bu-c denote cyclobutyl group,t-Bu and Bu-t denote tert-butyl group, Pen denotes pentyl group, c-Penand Pen-c denote cyclopentyl group, Hex denotes hexyl group, c-Hex andHex-c denote cyclohexyl group, Ph denotes phenyl group, and Naph denotesnaphthyl group.

In the Tables, aromatic heterocyclic rings represented by D-1-1b toD-32-3b have the following structures, respectively.

The numbers indicating the positions of the substituent (Z)_(n)correspond to the numbers in the above structural formulae, and in theTables, the aliphatic heterocyclic rings represented by E-2-2a toE-14-1a have the following structures, respectively.

In the Tables, partial saturated heterocyclic rings represented byM-4-2a and M-7-b have the following structures, respectively.

In the Tables, T-3 to T-6 have the following structures, respectively.

Further, in the Tables, the expression (R) or (S) in the columnsubstituent R² means that the proportion of the R-isomer or the S-isomeris at least 90% in a mixture ratio of optical isomers due to the carbonatom attached to R², and the expression (E) or (Z) in the columnsubstituent R¹ means that the proportion of the E-isomer or the Z-isomeris at least 90% in a mixture ratio of oxime geometrical isomers attachedto the substituent R¹. In the column m.p., “*1” means that the compoundwas oily or resinous.

TABLE 4

No. R² Y¹ Y² Y³ Y⁴ Y⁵ R¹ m.p. (° C.) 1-001 CH₃ H H F H H CH₃ 69.0-71.01-002 CH₃ H H F H H CH₂ (Ph-4-Cl) *1 1-003 H Cl H Cl H H CH₃ *1 1-004 HCl H Cl H H CH₃ (Z) 146.0-148.0 1-005 CH₃ Cl H Cl H H CH₃ *1 1-006 CH₃Cl H Cl H H i-Pr *1 1-007 CH₃ Cl H Cl H H CH₂CF₃ *1 1-008 CH₃ Cl H Cl HH CH₂ (Ph-4-Cl) *1 1-009 CH₃ CH₃ H OPr-i H H i-Pr *1 1-010 CH₃ CH₃ HOPr-i H H CH₂ (Ph-4-Cl) *1 1-011 CH₃ H H Br H H Et 95.0-96.0 1-012 CH₃ HH I H H Et 89.0-90.0 1-013 CH₃ H H t-Bu H H Et *1 1-014 CH₃ H H CF₃ H HEt 90.0-92.0 1-015 CH₃ H H CF₃ H H CH₂Pr-c 91.0-93.0 1-016 CH₃ H H CF₃ HH CH₂CF₃ 79.0-81.0 1-017 CH₃ H H CF₃ H H CH₂ (D-32-2b)-6-Cl 110.0-115.01-018 CH₃ H H OCF₃ H H Et 83.0-85.0 1-019 CH₃ H H OCF₃ H H CH ₂Pr-c59.0-61.0 1-020 CH₃ H H OPh H H Et *1 1-021 CH₃ H H OPh H H CH₂CF₃70.0-72.0 1-022 CH₃ H H OPh H H CH₂ (D-32-2b) -6-Cl *1 1-023 CH₃ H H PhH H Et *1 1-024 CH₃ H H Ph H H i-Pr *1 1-025 CH₃ H H Ph H H CH₂Pr-c *11-026 CH₃ H H Ph H H CH₂CF₃ 78.0-80.0 1-027 CH₃ H H Ph H H CH₂(D-32-2b)-6-Cl *1 1-028 CH₃ H F F F H Et 83.0-86.0 1-029 CH₃ H F F F HCH₂Pr-c 69.0-71.0 1-030 CH₃ H F F F H CH₂CF₃ 86.0-88.0 1-031 CH₃ H F F FH CH₂ (D-32-2h)-6-Cl 69.0-72.0 1-032 CH₃ H Cl Cl H H Et 73.0-75.0 1-033CH₃ H Cl Cl H H CH₂Pr-c 86.0-88.0 1-034 CH₃ H Cl Cl H H CH(CH₃)Ph *11-035 CH₃ H Br H CF₃ H Et *1 1-036 CH₃ H OPr-i H H H Et *1 1-037 CH₃ H—CH═CHCH═CH— H H Et *1 1-038 CH₃ H —CH═CHCH═CH— H H CH₂CF₃ *1 1-039 CH₃H —CH═CHCH═CH— H H CH₂ (D-32-2b)-6-Cl *1 1-040 CH₃ F H F H H Et74.0-76.0 1-041 CH₃ F H F H H CH₂Pr-c *1 1-042 CH₃ F H F H F CH₂Pr-c *11-043 CH₃ F H Cl H H Et *1 1-044 CH₃ F H Cl H H i-Pr *1 1-045 CH₃ F H BrH H Et *1 1-046 CH₃ F H Br H H i-Pr *1 1-047 CH₃ F H Br H H CH₂Pr-c *11-048 CH₃ F H Br H H CH₂CF₃ *1 1-049 CH₃ F H Br F H Et *1 1-050 CH₃ F HCF₃ H H Et *1 1-051 CH₃ F F F H H CH₃ *1 1-052 CH₃ F F F H H Et *1 1-053CH₃ Cl H H F H Et *1 1-054 CH₃ Cl H H Cl H Et *1 1-055 CH₃ Cl H H Cl HCH(CH₃)Ph *1 1-056 CH₃ Cl H H CF₃ H Et 64.0-66.0 1-057 CH₃ Cl H F H H Et*1 1-058 CH₃ Cl H Cl H H Et *1 1-059 H Cl H Cl H H i-Pr 71.0-73.0 1-060CH₃ Cl H Cl H H CH₂CH₂OCH₃ *1 1-061 CH₃ Cl H Cl H H CH₂(Ph-4-CN) *11-062 CH₃ Cl H Cl H H CH₂(D-1-1b)-5-CF₃ *1 1-063 CH₃ Cl H Cl H HCH₂(D-32-2b)-6-Cl *1 1-064 CH₃ Cl H Cl H H CH₂(D-32-3b)-2-Cl *1 1-065CH₃ Cl H Br H H Et *1 1-066 CH₃ Cl H Br H H i-Pr *1 1-067 CH₃ Cl H Br HH CH₂Pr-c *1 1-068 CH₃ Cl H Br H H CH₂CF₃ *1 1-069 CH, Cl H Br H HCH₂(D-32-2b)-6-Cl *1 1-070 CH₃ Cl H CH₃ H H CH₃ *1 1-071 CH₃ Cl H CH₃ HH Et *1 1-072 CH₃ Cl H CF₃ H H Et *1 1-073 CH₃ Cl H OCH₃ H H CH₃ *11-074 CH₃ Cl H OCH₃ H H Et *1 1-075 CH₃ Cl H SCH₃ H H Et *1 1-076 CH₃ ClH S(O)CH₃ H H Et *1 1-077 CH₃ Cl H SO₂CH₃ H H Et *1 1-078 CH₃ Cl HC(O)CH₃ H H Et *1 1-079 CH, Cl H C(CH₃)═NOCH₃ H H Et *1 1-080 CH₃ Cl HCN H H CH₃ *1 1-081 CH₃ Cl H CN H H Et *1 1-082 CH₃ Cl H (M-7-b)-4,4-(CH₃) ₂ H H Et 50.0-80.0 1-083 CH₃ Cl H CH═CH₂ H H CH₃ *1 1-084 CH₃ ClH CH═CH₂ H H Et *1 1-085 CH₃ Cl H Ph H H CH₃ *1 1-086 CH₃ Cl H Ph H H Et*1 1-087 CH₃ Cl H Ph-4-OCF₃ H H CH₃ *1 1-088 CH₃ Cl H Ph-4-OCF₃ H H Et*1 1-089 CH₃ Cl H D-3-a H H Et *1 1-090 CH₃ Cl H D-7-a H H Et *1 1-091CH₃ Cl H (D-7-b)-3-CF₃ H H Et *1 1-092 CH₃ Cl F H H H Et *1 1-093 CH₃ BrH F H H Et *1 1-094 CH₃ Br H F H H CH₂CH₂OCH₃ *1 1-095 CH₃ Br H F F H Et*1 1-096 CH₃ CH₃ H Cl H H Et *1 1-097 CH₃ CH₃ H CH₃ H H Et *1 1-098 CH₃CF₃ H Cl H H Et *1 1-099 CH₃ OCH₃ H Cl H H Et *1 1-100 CH₃ CH═NOEt H ClH H Et *1 1-101 CH₃ E-9-1a H Cl H H Et *1 1-102 CH₃ —CH═CHCH═CH— Br H HEt *1

TABLE 5

No. R² Y¹ Y² Y³ Y⁴ R¹ m.p. (° C.) 2-001 H H H CF₃ H CH₃ 128.0-130.02-002 H Cl H Cl H CH₃ *1 2-003 H Cl H Cl H Et *1 2-004 H Cl H Cl H n-Pr*1 2-005 H Cl H Cl H i-Pr *1 2-006 H Cl H Cl H n-Bu *1 2-007 H Cl H Cl Hi-Bu *1 2-008 H Cl H Cl H CH₂Pr-c *1 2-009 H Cl H Cl H s-Bu *1 2-010 HCl H Cl H c-Bu *1 2-011 H Cl H Cl H CH₂CF₃ *1 2-012 H Cl H Cl HCH₂CH═CH₂ *1 2-013 H Cl H Cl H CH₂ (Ph-4-Cl) *1 2-014 H Cl H CF₃ H CH₃*1 2-015 CH₃ Cl H CF₃ H CH₃ *1 2-016 H Cl H CF₃ H Et *1 2-017 H Cl H CF₃H n-Pr *1 2-018 H Cl H CF₃ H i-Pr 67.0-68.0 2-019 H Cl H CF₃ H i-Pr (E)81.0-83.0 2-020 H Cl H CF₃ H i-Pr (Z) 97.0-98.0 2-021 H Cl H CF₃ H i-Bu*1 2-022 H Cl H CF₃ H CH₂Pr-c *1 2-023 H Cl H CF₃ H CH₂Pr-c (E) 98.0-101.0 2-024 H Cl H CP ₃ H CH₂Pr-c (Z) 73.0-74.0 2-025 H Cl H CF₃ Hs-Bu *1 2-026 H Cl H CF₃ H c-Bu *1 2-027 H Cl H CF₃ H CH(Et) ₂ *1 2-028H Cl H CF₃ H CH(CH₃)Pr-c *1 2-029 H Cl H CF₃ H c-Pen *1 2-030 H Cl H CF₃H CH₂CHF₂ *1 2-031 H Cl H CF₃ H CH₂CHF₂ (E) *1 2-032 H Cl H CF₃ H CH₂CF₃*1 2-033 CH₃ Cl H CF₃ H CH₂CF₃ *1 2-034 H Cl H CF₃ H CH₂CH₂SCH₃ *1 2-035H Cl H CF₃ H CH₂(M-4-2a)CH₃ *1 2-036 H Cl H CF₃ H CH₂CN *1 2-037 H Cl HCF₃ H CH(CH₃)CN *1 2-038 H C1 H CF₃ H CH₂CH₂CN *1 2-039 H Cl H CF₃ HCH₂C(O)NHCH₂CF₃ *1 2-040 H C1 H CF₃ H CH₂CH═CH₂ *1 2-041 H Cl H CF₃ HCH₂C(CH₃)═CH₂ *1 2-042 H Cl H CF₃ H CH(CH₃)CH═CH₂ *1 2-043 H Cl H CF₃ HCH₂CH═C(CH₃)₂ 62.0-64.0 2-044 H Cl H CF₃ H CH₂C≡CH *1 2-045 H Cl H CF₃ HCH₂Ph 93.0-95.0 2-046 H Cl H CF₃ H CH₂(P6-2-F) *1 2-047 H Cl H CF₃ HCH₂(Ph-3-F) 65.0-70.0 2-048 H Cl H CF₃ H CH₂(Ph-4-F) *1 2-049 H Cl H CF₃H CH₂(Ph-2-Cl) 83.0-84.0 2-050 H Cl H CF₃ H CH₂(Ph-3-Cl) *1 2-051 H Cl HCF₃ H CH₂(Ph-4-Cl) *1 2-052 H Cl H CF₃ H CH₂(Ph-2-CH₃) 104.0-106.0 2-053H Cl H CF₃ H CH₂(Ph-3-CH₃) *1 2-054 H Cl H CF₃ H CH₂(Ph-4-CH₃) *1 2-055H Cl H CF₃ H CH₂ (Ph-4-Bu-t) *1 2-056 H Cl H CF₃ H CH₂(Ph-2-CF₃) *12-057 H Cl H CF₃ H CH₂(Ph-3-CF₃) *1 2-058 H Cl H CF₃ H CH₂(Ph-4-CF₃) *12-059 H Cl H CF₃ H CH₂(Ph-3-OCH₃) *1 2-060 H Cl H CF₃ H CH₂(Ph-4-OCH₃)*1 2-061 H Cl H CF₃ H CH₂(Ph-2-OCF₃) *1 2-062 H Cl H CF₃ HCH₂(Ph-3-OCF₃) *1 2-063 H Cl H CF₃ H CH₂(Ph-4-OCF₃) *1 2-064 H Cl H CF₃H CH₂(Ph-4-NO₂) *1 2-065 H Cl H CF₃ H CH₂(Ph-2-CN) *1 2-066 H Cl H CF₃ HCH₂(Ph-3-CN) *1 2-067 H Cl H CF₃ H CH₂(Ph-4-CN) *1 2-068 H Cl H CF₃ HCH₂(Ph-4-Ph) *1 2-069 H Cl H CF₃ H CH₂(Ph-2,4-F₂) *1 2-070 H Cl H CF₃ HCH₂(Ph-2,6-F₂) 86.0-88.0 2-071 H Cl H CF₃ H CH₂(Ph-3,4-F₂) *1 2-072 H ClH CF₃ H CH₂(Ph-3,5-P₂) *1 2-073 H Cl H CF₃ H CH₂(Ph-3,4-Cl₂) *1 2-074 HCl H CF₃ H CH₂(Ph-3,4,5-F₃) *1 2-075 H Cl H CF₃ H CH₂(2-Naph) *1 2-076 HCl H CF₃ H CH₂(D-5-3b)-3-CH₃ 95.0-97.0 2-077 H Cl H CF₃ H CH₂(D-32-1a)*1 2-078 H Cl H CF₃ H CH₂(D-32-2a) *1 2-079 H Cl H CF₃ HCH₂(D-32-2b)-6-Cl *1 2-080 H Cl H CF₃ H CH₂(D-32-3a) *1 2-081 H Cl H CF₃H CH(CH₃)Ph *1 2-082 H Cl H CF₃ H CH₂CH₂Ph 106.0-108.0 2-083 H Cl H OCH₃H CH₃ *1 2-084 H OCH₃ H Cl H CH₃ *1 2-085 H F H Cl H i-Pr *1 2-086 H ClH Cl H c-Pen *1 2-087 H Cl H Cl H CH₂CH₂Cl *1 2-088 H Cl H Cl HCH(CH₃)OEt *1 2-089 H Cl H Cl H E-14-1a *1 2-090 H Cl H Cl H CH₂(E-9-1a) *1 2-091 H Cl H Cl H CH₂CH₂SCH₃ *1 2-092 H Cl H Cl HCH₂Si(CH₃)₃ *1 2-093 H Cl H Cl H CH₂C(CH₃)═NOCH₃ *1 2-094 H Cl H Cl HCH₂CN *1 2-095 H Cl H Cl H CH₂C(O)OCH, *1 2-096 H Cl H Cl HCH(CH₃)CH═CH₂ *1 2-097 H Cl H Cl H CH₂CCl═CHCl *1 2-098 H Cl H Cl HCH₂(Ph-2-F) *1 2-099 H Cl H Cl H CH₂(Ph-3-F) *1 2-100 H Cl H Cl HCH₂(Ph-4-F) *1 2-101 H Cl H Cl H CH₂(Ph-2-Cl) *1 2-102 H Cl H Cl HCH₂(Ph-3-Cl) *1 2-103 H Cl H Cl H CH₂(Ph-4-SCF₃) *1 2-104 H Cl H Cl HCH₂(Ph-4-CN) *1 2-105 H Cl H Cl H CH₂ (Ph-3,4-F₂) *1 2-106 H Cl H Cl ClEt *1 2-107 H Cl H Cl Cl i-Pr *1 2-108 H Cl H Cl Cl CH₂Pr-c *1 2-109 HCl H Cl Cl CH₂CH═CH₂ *1 2-110 H Cl H Cl Cl CH₂(Ph-4-F) *1 2-111 H Cl HCH₂OCH₃ H i-Pr *1 2-112 H F H F H i-Pr *1 2-113 H F H Cl H Et *1 2-114 HCl H Cl H CH₃ (Z) 88.0-89.0 2-115 CH₃ Cl H Cl H CH₃ *1 2-116 CH₃ (S) ClH Cl H CH₃ *1 95% e.e. [ α ]_(D) ^(19.0)−13.70° (EtOH, c = 0.10) 2-117CH₃ Cl H Cl H CH₃ (Z) 104.0-105.0 2-118 CH₃ (S) Cl H Cl H CH₃ (Z) *1 95%e.e. [ α ]_(D) ^(21.7)−12.50° (EtOH, c = 0.10) 2-119 Et Cl H Cl H CH₃ *12-120 H Cl H Cl H Et (Z) 84.0-86.0 2-121 CH₃ Cl H Cl H Et *1 2-122 CH₃(S) Cl H Cl H Et *1 95% e.e. [ α ]_(D) ^(19.0)−13.10° (EtOH, c = 0.10)2-123 CH₃ Cl H Cl H Et (Z) *1 2-124 CH₃ (S) Cl H Cl H Et (Z) *1 95% e.e.[ α ]_(D) ^(21.7)−11.40° (EtOH, c = 0.10) 2-125 t-Bu Cl H Cl H Et *12-126 H Cl H Cl H n-Pr (Z) 80.0-83.0 2-127 CH₃ Cl H Cl H n-Pr (Z) *12-128 H Cl H Cl H i-Pr (Z) 107.0-108.0 2-129 CH₃ Cl H Cl H i-Pr *1 2-130CH₃ (S) Cl H Cl H i-Pr *1 95% e.e. [ α ]_(D) ^(19.0)−13.20° (EtOH, c =0. 10) 2-131 CH₃ Cl H Cl H i-Pr (Z) *1 2-132 CH₃ (S) Cl H Cl H i-Pr (Z)*1 95% e.e. [ α ]_(D) ^(21.8)−8.60° (EtOH, c = 0.10) 2-133 H Cl H Cl Hn-Bu (Z) 80.0-84.0 2-134 H Cl H Cl H i-Bu (Z) 91.0-93.0 2-135 H Cl H ClH CH₂Pr-c (Z) 119.0-121.0 2-136 H Cl H Cl H s-Bu (Z) 68.0-70.0 2-137 CH₃Cl H Cl H s-Bu (Z) *1 2-138 H Cl H Cl H c-Bu (Z) 100.0-102.0 2-139 H ClH Cl H t-Bu *1 2-140 H Cl H Cl H t-Bu (Z) *1 2-141 H Cl H Cl H Pen *12-142 H Cl H Cl H Pen (Z) 79.0-80.0 2-143 H Cl H Cl H CH₂Bu-c 72.0-75.02-144 H Cl H Cl H CH(Et)₂ *1 2-145 H Cl H Cl H c-Pen (Z)  99.0-100.02-146 H Cl H Cl H Hex *1 2-147 H Cl H Cl H CH₂Pen-c 75.0-78.0 2-148 H ClH Cl H c-Hex 73.0-76.0 2-149 H Cl H Cl H CH₂Hex-c *1 2-150 H Cl H Cl HCH₂CHF₂ *1 2-151 CH₃ Cl H Cl H CH₂CF₃ (Z) *1 2-152 H Cl H Cl HCH₂CH₂OCH₃ *1 2-153 H Cl H Cl H E-2-2a *1 2-154 H Cl H Cl H CH₂(E-5-1a)74.0-77.0 2-155 H Cl H Cl H CH₂(E-5-2a) *1 2-156 H Cl H Cl H CH₂C(O)OEt*1 2-157 H Cl H Cl H CH₂CH═CH₂ (Z) 78.0-82.0 2-158 CH₃ Cl H Cl HCH₂CH═CH₂ (Z) *1 2-159 H Cl H Cl H CH₂CCl═CH₂ *1 2-160 H Cl H Cl HCH₂C≡CH *1 2-161 H Cl H Cl H CH₂Ph *1 2-162 H Cl H Cl H CH₂(Ph-4-OCH₃)*1 2-163 H Cl H Cl H CH₂(Ph-2-CN) *1 2-164 H Cl H Cl H CH₂(D-10-1a) *12-165 H Cl H Cl H CH₂(D-10-2a) *1 2-166 H Cl H Cl H CH₂(D-10-2b)-2-Cl *12-167 H Cl H Cl H CH₂(D-10-3b)-2-Cl *1 2-168 H Cl H Cl HCH₂(D-32-2b)-6-Cl *1 2-169 H Cl H Cl H CH₂(D-32-3b)-2-Cl *1 2-170 H Cl HCl H CH₂(D-32-3b)-2,6-Cl₂ 155.0-165.0 2-171 H Cl H Cl H CH(CH₃)Ph *12-172 H Cl H Cl H CH(CH₃)Ph (Z) *1 2-173 H Cl H Cl H CH(CH₃)(Ph-4-F) *12-174 H Cl H Cl H CH(CH₃)(Ph-4-F) (Z) *1 2-175 H Cl H Cl H C(CH₃)₂Ph *12-176 H Cl H Cl H CH₂CH₂Ph *1 2-177 H Cl H Cl H Ph *1 2-178 H Cl H Cl FEt *1 2-179 H Cl H Cl F i-Pr *1 2-180 H Cl H Cl OCH₃ i-Pr *1 2-181 H ClH Br H i-Pr *1 2-182 H Cl H Br H i-Pr (Z) 109.0-111.0 2-183 H Cl H CF₃ HCH₃ (Z) 113.0-117.0 2-184 CH₃ Cl H CF₃ H CH₃ (Z) *1 2-185 H Cl H CF₃ HEt (Z) 60.0-62.0 2-186 CH₃ Cl H CF₃ H Et (Z) *1 2-187 H Cl H CF₃ H n-Pr(Z) 71.0-72.0 2-188 CH₃ Cl H CF₃ H i-Pr (Z) *1 2-189 H Cl H CF₃ H n-Bu(Z) 88.0-89.0 2-190 H Cl H CF₃ H i-Bu (Z) 84.0-85.0 2-191 H Cl H CF₃ Hs-Bu (Z) 79.0-82.0 2-192 H Cl H CF₃ H Pen (Z) 87.0-89.0 2-193 H Cl H CF₃H c-Pen (Z) 106.0-108.0 2-194 H Cl H CF₃ H CH₂CH═CH₂ (Z) 49.0-50.0 2-195H Cl H CF₃ H CH(CH₃)Ph (Z) *1 2-196 H Cl H CF₃ H CH(CH₃)(Ph-4-F) (Z) *12-197 H Cl H OCH₃ H i-Pr *1 2-198 H Cl H C(CH₃)═NOCH₃ H i-Pr *1 2-199 HCl H CN H Et *1 2-200 H Cl H CN H i-Pr *1 2-201 H Cl H CN H CH₂Pr-c *12-202 H Cl H CN H CH(CH₃)Ph *1 2-203 H CF₃ H CF₃ H i-Pr 60.0-65.0 2-204H Cl H F H n-Pr *1 2-205 H Cl H F H i-Pr (Z)  99.0-101.0 2-206 Ph Cl HCl H CH₃ (Z) *1 2-207 CH₃ Cl H Cl H n-Bu (Z) *1 2-208 CH₃ Cl H Cl H i-Bu(Z) *1 2-209 CH₃ Cl H Cl H CH₂Pr-c (Z) *1 2-210 CH₃ Cl H Cl H t-Bu (Z)*1 2-211 H Cl H Cl H CH (Et)₂ (Z) *1 2-212 H Cl H Cl H CH₂CF₃ (Z)100.0-102.0 2-213 H Cl H Cl H CH(CH₃)CH═CH₂ (Z) *1 2-214 H Cl H Cl F Et(Z) *1 2-215 H Cl H Cl F i-Pr (Z) 122.0-125.0 2-216 H Cl H Br H CH₃ (Z)85.0-86.0 2-217 H Cl H Br H Et (Z) 101.0-102.0 2-218 H CI H CH₃ H i-Pr(Z) 117.0-119.0 2-219 H Cl H CF₃ H CH(Et)₂ (Z) *1 2-220 H Cl H CF₃ HCH(CH₃)CH═CH₂ (Z) *1 2-221 H Cl H CF₃ H CH₂(Ph-4-CN) (Z) 139.0-141.02-222 H Cl H OCHF₂ H CH₃ *1 2-223 H Cl H OCH₂CF₃ H CH₃ *1 2-224 H Cl HCH═CH₂ H i-Pr *1 2-225 H Cl H C≡CH H i-Pr (Z) 104.0-105.0 2-226 H Cl HC≡CSi(CH₃)₃ H i-Pr (Z) *1 2-227 H Cl H D-3-a H i-Pr *1 2-228 H Cl HD-7-a H i-Pr *1 2-229 H Cl H D-22-a H i-Pr *1 2-230 H Cl Cl Cl H CH₃ (Z)129.0-130.0 2-231 H Cl Cl Cl H Et (Z) 100.0-101.0 2-232 H Cl CN Cl Hi-Pr *1 2-233 H Br H Br H CH₃ 65.0-75.0 2-234 CH₃ Br H Br H CH₃ (Z) *12-235 H Br H Br H Et *1 2-236 H Br H Br H Et (Z) *1 2-237 CH₃ Br H Br HEt (Z) *1 2-238 H Br H Br H n-Pr *1 2-239 H Cl H Cl H i-Pr (E) 54.0-57.02-240 H Cl H Cl H CH₂CHF₂ (Z) 58.0-62.0 2-241 H Cl H Cl H CH₂(Ph-4-F)(Z) 105.0-109.0 2-242 H Cl H Cl H CH₂(Ph-4-Cl) (Z) *1 2-243 H Cl H Cl HCH₂(Ph-3,4-F₂) (Z) *1 2-244 H Cl H Br H CH(CH₃)Ph (Z) *1 2-245 H Cl HCF₃ H CH₂(Ph-3,4-F₂) (Z) 96.0-98.0 2-246 H Cl H CF₃ H CH₂ (Ph-3,4,5-F₃)(Z) 100.0-103.0 2-247 H Cl H O(Ph-4-Cl) H CH₃ *1 2-248 H Cl H C≡CBu-t Hi-Pr *1 2-249 H Cl H C≡CPh H i-Pr *1 2-250 H Br H Br H i-Pr (Z)113.0-115.0 2-251 H Br H Br H CH₂CF₃ *1 2-252 H Cl H H H CH₃ (Z)95.0-98.0 2-253 H Cl H H H i-Pr (Z)  99.0-102.0 2-254 CH₃ (S) Cl H Cl Hn-Pr (Z) *1 83% e.e. [ α ]_(D) ^(26.1)−9.42° (EtOH, c = 0.10) 2-255 H ClH O(Ph-4-Cl) H i-Pr *1 2-256 H Cl H C≡CCH₃ H i-Pr *1 2-257 H Cl HC≡CPr-c H i-Pr (Z) *1 2-258 H Cl H C≡CPen-c H i-Pr *1 2-259 H Cl H C≡CClH i-Pr *1 2-260 H Cl H C≡CBr H i-Pr *1 2-261 H Cl H C≡CI H i-Pr *1 2-262H Cl H C≡CC(CH₃)₂OH H i-Pr *1 2-263 H Cl H C≡C (T-3) H i-Pr *1 2-264 HCl H C≡C (T-4) H i-Pr *1 2-265 H Cl H C≡C (T-5) H i-Pr *1 2-266 H Cl HC≡C (T-6) H i-Pr *1 2-267 H Cl H C≡C (Ph-4-Bu-t) H i -Pr *1 2-268 H Cl HC≡C (D-32-1a) H i-Pr *1 2-269 H Cl H C≡C(D-32-2a) H i -Pr *1 2-270 H ClH C≡C (D-32-3a) H i-Pr *1 2-271 H Cl H Ph-4-F H i-Pr *1

TABLE 6

No. X¹ X² X⁴ X⁵ R² Y¹ Y³ A R¹ m.p. (° C.) 3-001 F F H H CH₃ H F CH CH₃58.0-61.0 3-002 F F H H CH₃ H F CH CH₂(Ph-4-Cl) *1 3-003 CH₃ H H H CH₃Cl Cl CH CH₃ *1 3-004 F H H H H Cl Cl N Et *1 3-005 F F H H H Cl Cl N Et*1 3-006 Cl H H H H Cl Cl N Et *1 3-007 Cl H H H H Cl Cl N n-Pr (Z) *13-008 Cl F H H H Cl Cl N Et *1 3-009 Cl Cl H H H Cl Cl N Et *1 3-010 BrH H H H Cl Cl N Et *1 3-011 Br H H H H Cl Cl N n-Pr (Z) *1 3-012 I H H HCH₃ H Br CH Et 106.0-109.0 3-013 I H H H CH₃ Cl Cl CH Et *1 3-014 I H HH H Cl Cl N Et *1 3-015 I H H H H Cl Cl N n-Pr (Z) *1 3-016 I H H H H ClCl N i-Pr *1 3-017 I H H H H Cl Cl N CH₂Pr-c *1 3-018 I H H H H Cl Cl NCH(CH₃)Ph *1 3-019 CH₃ H H H H Cl Cl N n-Pr (Z) *1 3-020 CH₃ H H H H ClCl N i-Pr *1 3-021 CH₃ H H F H Cl Cl N Et *1 3-022 CHF₂ H H H H Cl Cl NEt 93.0-95.0 3-023 CHF₂ H H H H Cl Cl N i-Pr *1 3-024 CF₃ H F H H Cl ClN i-Pr *1 3-025 CF₃ F H H H Cl Cl N Et *1 3-026 OCH₃ H H H H Cl Cl N Et*1 3-027 OCHF₂ H H H H Cl Cl N Et *1 3-028 OCF₃ H H H H Cl Cl N Et *13-029 SCH₃ H H H H Cl Cl N Et *1 3-030 NO₂ H H H H Cl Cl N Et *1 3-031CN H H H H Cl Cl N Et *1 3-032 Ph H H H H Cl Cl N Et *1 3-033 Cl H H H HCl Cl N CH₃ *1 3-034 Cl H H H H Cl Cl N s-Bu (Z) 74.0-79.0 3-035 Cl H HH H Cl Cl N t-Bu (Z) *1 3-036 Cl H H H H Cl Cl N CH₂CF₃ (Z) 93.0-94.03-037 Br H H H H Cl Cl N CH₃ (Z) *1 3-038 Br H H H H Cl Cl N s-Bu (Z) *13-039 Br H H H H Cl Cl N t-Bu (Z) *1 3-040 Br H H H H Cl Cl N CH₂CF₃ (Z)*1 3-041 Br H H H H Cl Cl N CH(CH₃)(Ph-4-F) (Z) 68.0-72.0 3-042 I H H HH Cl Cl N CH₃ *1 3-043 I H H H H Cl Cl N s-Bu (Z) *1 3-044 I H H H H ClCl N t-Bu *1 3-045 I H H H H Cl Cl N CH₂CF₃ *1 3-046 CH₃ H H H H Cl Cl NCH₃ *1 3-047 CH₃ H H H H Cl Cl N s-Bu (Z) 76.0-79.0 3-048 CH₃ H H H H ClCl N t-Bu (Z) *1 3-049 CH₃ H H H H Cl Cl N CH₂CF₃ 86.0-87.0 3-050 CH₃ HH H H Cl Cl N CH(CH₃)(Ph-4-F) (Z)  95.0-100.0 3-051 CH₃ H H H H Br Br NCH₂CF₃ *1

TABLE 7

m.p. No. X¹ R⁴ R² R³ Y¹ Y³ R¹ (° C.) 4-001 I H CH₃ CH₃ Cl Cl CH₃ *14-002 CF₃ H CH₃ CH₃ Cl Cl Et (Z) *1 4-003 CF₃ H —CH₂CH₂— Cl Cl Et (Z)104.0- 105.0 4-004 CF₃ H —CH₂CH₂CH₂— Cl Cl Et *1 4-005 CF₃ CH₃ H H Cl ClCH₃ *1 4-006 CF₃ Et H H Cl Cl CH₃ *1 4-007 CF₃ c-Pr H H Cl Cl CH₃ 75.0-77.0 4-008 CF₃ CH₂OCH₃ H H Cl Cl CH₃ *1 4-009 CF₃ CH₂CH═CH₂ H H Cl ClCH₃ *1 4-010 CF₃ CH₂CH≡CH H H Cl Cl CH₃ *1 4-011 CF₃ c-Pr H H Cl CF₃ CH₃*1 4-012 CF₃ CH₂CN H H Cl Cl CH₃ *1 4-013 CF₃ C(O)CH₃ H H Cl Cl CH₃ *14-014 CF₃ C(O)OCH₃ H H Cl Cl CH₃ *1 4-015 CF₃ SCCl₃ H H Cl Cl CH₃ *1

TABLE 8

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m p. (° C.) 5-001 CF₃ H Cl H Br H N CH₃ *1

TABLE 9

No. X¹ X⁴ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 6-001 Cl H H Cl H Cl H N Et *16-002 Cl CF₃ H Cl H Cl H N Et 49.0-55.0 6-003 Br H H Cl H Cl H N Et *16-004 CH₃ H H Cl H Cl H N Et *1 6-005 CF₃ H H Cl H Cl H N Et (Z) *16-006 Cl H H Cl H Cl H N i-Pr (Z) *1 6-007 Br H H Cl H Cl H N i-Pr (Z)*1 6-008 CF₃ H H Cl H Cl H N i-Pr (Z) *1

TABLE 10

m.p. No. X¹ X⁴ R² Y¹ Y² Y³ Y⁴ A R¹ (° C.) 7-001 Cl H H Cl H Cl H CH CH₃*1 7-002 Cl H H Cl H Cl H N Et *1 7-003 Br CF₃ H Cl H Cl H N Et *1 7-004CF₃ H CH₃ Cl H Cl H CH Et *1 7-005 CF₃ H H Cl H Cl H N Et 97.0- 99.07-006 Cl H H Cl H Cl H N CH₃ (Z) *1 7-007 Cl H H Cl H Cl H N n-Pr (Z) *17-008 Cl H H Cl H Cl H N t-Bu (Z) *1 7-009 Cl H H Cl H Cl H N CH₂CF₃ (Z)*1

TABLE 11

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 8-001 CF₃ H Cl H Cl H N Et (Z) *1

TABLE 12

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 9-001 CF₃ H Cl H Cl H N CH₃ (Z)*1 9-002 CF₃ CH₃ Cl H Cl H CH Et (Z) *1 9-003 CF₃ H Cl H Cl H N Et90.0-92.0 9-004 CF₃ H Cl H Cl H N CH₂Pr-c *1 9-005 CF₃ H Cl H Cl H Nt-Bu (isomerA) *1 9-006 CF₃ H Cl H Cl H N t-Bu (isomerB) *1 9-007 CF₃ HCl H Cl H N i-Pr (Z) *1

TABLE 13

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 10-001 Br H Cl H Cl H N Et *110-002 CH₃ H Cl H Cl H N Et (Z) *1

TABLE 14

No. X¹ X³ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 11-001 CH₃ CH₃ H Cl H Cl H NEt *1 11-002 CF₃ CH₃ H Cl H Cl H N Et *1 11-003 CF₃ Ph H Cl H Cl H N Et*1

TABLE 15

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 12-001 CH₃ CH₃ H H F H CH CH₃ *112-002 CH₃ CH₃ H H F H CH CH₂(Ph-4-Cl) *1 12-003 CH₃ H Cl H Cl H CH CH₃*1 12-004 CH₃ CH₃ Cl H Cl H CH CH₃ 75.0-77.0 12-005 CH₃ CH₃ Cl H Cl H CHi-Pr *1 12-006 CH₃ CH₃ Cl H Cl H CH CH₂(Ph-4-Cl) *1 12-007 CH₃ H Cl HCF₃ H N i-Pr *1 12-008 Br H Cl H Cl H N Et *1 12-009 I H Cl H Cl H N Et*1 12-010 CH₃ H Cl H Cl H N Et *1 12-011 CF₃ H Cl H Cl H N Et *1 12-012CH₃ H Cl H Cl H N CH₃ *1 12-013 CH₃ H Cl H Cl H N n-Pr *1 12-014 CH₃ HCl H Cl H N s-Bu (E) *1 12-015 CH₃ H Cl H Cl H N s-Bu (Z) 56.0-61.012-016 CH₃ H Cl H Cl H N t-Bu (Z) *1 12-017 CH₃ H Cl H Cl H N CH₂CF₃ *112-018 CF₃ CH₃ (S) Cl H Cl H N n-Pr (Z) *1 83% e.e. [ α ]_(D)^(25.6)−7.32° (EtOH, c = 0.10) 12-019 CF₃ H Cl H Cl H N i-Pr 46.0-50.012-020 CF₃ H Cl H CF₃ H N n-Pr (Z) *1

TABLE 16

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 13-001 I H Cl H Cl H N Et *113-002 CF₃ H Cl H Cl H N Et *1 13-003 I CH₃ (S) Cl H Cl H N n-Pr (Z) *183% e. e. [α]_(D) ^(25.9) − 25.10° (EtOH, c = 0.10)

TABLE 17

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 14-001 I H Cl H Cl H N Et *1

TABLE 18

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 15-001 CF₃ H Cl H Cl H N Et (Z)*1 15-002 CF₃ H Cl H Cl H N i-Pr (Z) *1

TABLE 19

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 16-001 CF₃ H Cl H Cl H N Et (Z)112.0-113.0

TABLE 20

No. X¹ X² R⁴ R² Y¹ Y³ A R¹ m p. (° C.) 17-001 Cl Cl H H Cl Cl N Et *117-002 CHF₂ H H H Cl Cl CH CH₃ *1 17-003 CHF₂ H H CH₃ Cl Cl CH CH₃ *117-004 CHF₂ H H H Cl Cl N Et *1 17-005 CF₃ H H H Cl Cl CH CH₃ *1 17-006CF₃ H H H Cl Cl N Et *1 17-007 CF₃ H H H Cl CF₃ N CH₃ 105.0-110.0 17-008CF₃ F H H Cl Cl N CH₃ (Z) *1 17-009 CF₃ F c-Pr H Cl Cl N CH₃ 95.0-97.017-010 CF₃ F H H Cl Cl N Et (Z) 88.0-90.0 17-011 CHF₂ H H H Cl Cl N i-Pr(Z) *1 17-012 CHF₂ H H H Cl CF₃ N n-Pr (Z) *1

TABLE 21

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 18-001 CF₃ H Cl H Cl H N Et (Z)*1

TABLE 22

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 19-001 CH₃ H Cl H Cl H N Et *1

TABLE 23

No. X¹ X³ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 20-001 CHF₂ CH₃ H Cl H Cl H NEt *1 20-002 CF₃ CH₃ CH₃ Cl H Cl H CH Et *1 20-003 CF₃ GH₃ H Cl H Cl H NEt *1 20-004 CF₃ CH₃ H Cl H Cl H N CH₂Pr-c (Z) *1 20-005 CF₃ CH₃ H Cl HCl H N CH(CH₃)Ph *1 20-006 CF₃ CH₃ H Cl H Cl H N CH₂CF₃ (Z) 127.0-128.020-007 CF₃ CF₃ H Cl H Cl H N Et  98.0-103.0

TABLE 24

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 21-001 CF₃ H Cl H Cl H N Et (Z)*1

TABLE 25

No. X¹ R² Y¹ Y² Y³ Y⁴ A R¹ m.p. (° C.) 22-001 CF₃ CH₃ Cl H Cl H CH Et *122-002 CF₃ H Cl H Cl H N Et *1 22-003 CF₃ H Cl H Cl H N i-Pr *1

TABLE 26

No. X¹ R² Y¹ Y³ Y⁴ Y⁵ R¹ m.p. (° C.) 23-001 CF₃ H Cl H Cl H Et 84.0-86.023-002 CF₃ H Cl H Cl H i-Pr 75.0-77.0 23-003 CF₃ H Cl H Cl H c-Pen89.0-91.0 23-004 CF₃ H Cl H Cl H CH₂ (Ph-4-F) *1 23-005 CF₃ H Cl Cl H HCH₃ 124.0-126.0

TABLE 27

No. X¹ R² Y¹ Y³ Y⁴ R¹ m.p. (° C.) 24-001 CF₃ H Cl Cl H i-Pr *1

TABLE 28

No. X¹ R² Y¹ Y² Y³ R¹ m.p. (° C.) 25-001 CF₃ H Cl Cl Cl CH₃ 95.0-100.025-002 CF₃ H Cl Cl Cl Et 95.0-100.0 25-003 CF₃ H Cl Cl Cl n-Pr75.0-78.0  25-004 CF₃ H Cl Cl Cl i-Pr 98.0-102.0

TABLE 29

No. X¹ R² Y¹ Y³ Y⁴ R¹ m.p. (° C.) 26-001 CF₃ CH₃ Cl H H Et *1 26-002 CF₃CH₃ Cl H H CH(CH₃)Ph *1 26-003 CF₃ CH₃ Cl Cl H Et *1

TABLE 30

No. X¹ R² Y¹ Y² R⁵ R¹ m.p. (° C.) 27-001 CF₃ CH₃ Cl OPr-i CH₃ CH₃ (E) *127-002 CF₃ CH₃ Cl OPr-i CH₃ CH₃ (Z) *1

TABLE 31

No. X¹ R² Y¹ R⁵ Y⁴ R¹ m. p. (° C.) 28-001 CF₃ CH₃ CF₃ CH₃ H Et129.0-131.0

TABLE 32

No. X¹ R² Y¹ Y³ R¹ m. p. (° C.) 29-001 CF₃ H Cl Cl CH₃ *1 29-002 CF₃ HCl Cl Et *1

TABLE 33

No. X¹ R² Y¹ Y² Y³ Y⁴ A m. p. (° C.) 30-001 CF₃ CH₃ H H CF₃ H CH174.0-175.0 30-002 CF₃ CH₃ H H OCF₃ H CH 111.0-113.0 30-003 CF₃ CH₃ H HOPh H CH 118.0-120.0 30-004 CF₃ CH₃ H H Ph H CH 151.0-153.0 30-005 CF₃CH₃ H F F F CH 174.0-175.0 30-006 CF₃ CH₃ H Cl Cl H CH 157.0-160.030-007 CF₃ CH₃ H —CH═CHCH═CH— H CH *1 30-008 CF₃ CH₃ F H F H CH132.0-134.0 30-009 CF₃ CH₃ F H F H CF *1 30-010 CF₃ H F H F H N *130-011 CF₃ CH₃ F H Cl H CH 144.0-145.0 30-012 CF₃ H F H Cl H N *1 30-013CF₃ CH₃ F H Br H CH *1 30-014 CF₃ CH₃ F H Br H CF *1 30-015 CF₃ CH₃ Cl HH Cl CH 158.0-160.0 30-016 CF₃ CH₃ Cl H Cl H CH *1 30-017 CF₃ H Cl H ClH N 134.0-136.0 30-018 CF₃ CH₃ Cl H Cl H N *1 30-019 CF₃ H Cl H Cl F N*1 30-020 CF₃ H Cl H Cl OCH₃ N *1 30-021 CF₃ CH₃ Cl H Br H CH *1 30-022CF₃ H Cl H Br H N *1 30-023 CF₃ H Cl H CF₃ H N 110.0-113.0 30-024 CF₃ HCl H C(CH₃)═NOCH₃ H N *1 30-025 CF₃ H Cl H CN H N *1 30-026 CF₃ CH₃ Br HF H CH 48.0-50.0 30-027 CF₃ CH₃ CH₃ H Cl H CH 132.0-133.0 30-028 CF₃ HCF₃ H CF₃ H N *1

TABLE 34

m. p. No. X¹ R² Y¹ Y² Y³ Y⁴ A (° C.) 31-001 CF₃ H F H F H N *1 31-002CF₃ H F H Cl H N *1 31-003 CF₃ H Cl H Cl H N *1 31-004 CF₃ H Cl H Cl F N*1 31-005 CF₃ H Cl H Cl OCH₃ N *1 31-006 CF₃ H Cl H Br H N *1 31-007 CF₃H Cl H CF₃ H N 100.0- 102.0 31-008 CF₃ H Cl H C(CH₃)═NOCH₃ H N *1 31-009CF₃ H Cl H CN H N *1 31-010 CF₃ H CF₃ H CF₃ H N *1

TABLE 35

No. X¹ R² Y¹ Y² Y³ Y⁴ A m. p. (° C.) 32-001 I CH₃ H H Br H CH140.0-144.0 32-002 I H Cl H Cl H N 109.0-110.0 32-003 CF₃ CH₃ H H I H CH127.0-128.0 32-004 CF₃ CH₃ H H t-Bu H CH *1 32-005 CF₃ CH₃ H H CF₃ H CH107.0-108.0 32-006 CF₃ CH₃ H H OCF₃ H CH 88.0-89.0 32-007 CF₃ CH₃ H HOPh H CH 103.0-105.0 32-008 CF₃ CH₃ H H Ph H CH 167.0-168.0 32-009 CF₃CH₃ H F F F CH 128.0-129.0 32-010 CF₃ CH₃ H Cl Cl H CH 128.0-129.032-011 CF₃ CH₃ H Br H CF₃ CH *1 32-012 CF₃ CH₃ H OPr-i H H CH *1 32-013CF₃ CH₃ H —CH═CHCH═CH— H CH *1 32-014 CF₃ CH₃ F H F H CH 67.0-69.032-015 CF₃ CH₃ F H F H CF *1 32-016 CF₃ CH₃ F H Cl H CH 73.0-74,0 32-017CF₃ CH₃ F H Br H CH 89.0-90.0 32-018 CF₃ CH₃ F H Br H CF *1 32-019 CF₃CH₃ F H Br F CH *1 32-020 CF₃ CH₃ F H CF₃ H CH 80.0-81.0 32-021 CF₃ CH₃F F F H CH 107.0-108.0 32-022 CF₃ CH₃ Cl H H F CH 67.0-69.0 32-023 CF₃CH₃ Cl H H Cl CH 88.0-90.0 32-024 CF₃ CH₃ Cl H H CF₃ CH *1 32-025 CF₃CH₃ Cl H F H CH *1 32-026 CF₃ CH₃ Cl H Cl H CH 52.0-53.0 32-027 CF₃ H ClH Cl H N 123.0-125.0 32-028 CF₃ CH₃ Cl H Cl H N 85.0-89.0 32-029 CF₃ CH₃Cl H Br H CH *1 32-030 CF₃ CH₃ Cl H CH₃ H CH *1 32-031 CF₃ CH₃ Cl H CF₃H CH *1 32-032 CF₃ H Cl H CF₃ H N *1 32-033 CF₃ CH₃ Cl H OCH₃ H CH *132-034 CF₃ CH₃ Cl H SCH₃ H CH *1 32-035 CF₃ CH₃ Cl H CN H CH *1 32-036CF₃ CH₃ Cl H C(O)OCH₂C(CH₃)₂NH₂•HCl H CH 135.0-137.0 32-037 CF₃ CH₃ Cl H(M-7-b)-4,4-(CH₃)₂ H CH *1 32-038 CF₃ CH₃ Cl H CH═CH₂ H CH *1 32-039 CF₃CH₃ Cl H C≡CSi(CH₃)₃ H CH *1 32-040 CF₃ CH₃ Cl H Ph H CH *1 32-041 CF₃CH₃ Cl H Ph-4-OCF₃ H CH *1 32-042 CF₃ CH₃ Cl H D-3-a H CH *1 32-043 CF₃CH₃ Cl H D-7-a H CH *1 32-044 CF₃ CH₃ Cl H (D-7-b)-3-CF₃ H CH *1 32-045CF₃ CH₃ Cl F H H CH 50.0-51.0 32-046 CF₃ CH₃ Br H F H CH *1 32-047 CF₃CH₃ Br H F F CH *1 32-048 CF₃ CH₃ CH₃ H Cl H CH *1 32-049 CF₃ CH₃ CF₃ HCl H CH *1 32-050 CF₃ CH₃ OCH₃ H Cl H CH 90.0-92.0 32-051 CF₃ CH₃ E-9-1aH Cl H CH *1 32-052 CF₃ CH₃ —CH═CHCH═CH— Br H CH *1 32-053 CF₃ Ph Cl HCl H N 164.0-166.0 32-054 CF₃ H Cl Cl Cl H N 124.0-125.0 32-055 CF₃ H ClCN Cl H N *1 32-056 CF₃ H Br H Br H N *1 32-057 CF₃ CH₃ Br H Br H N *1

TABLE 36

No. X¹ R² Y¹ Y³ Y⁴ m. p. (° C.) 33-001 CF₃ H Cl Cl H *1

TABLE 37

No. X¹ R² Y¹ Y² Y³ m. p. (° C.) 34-001 CF₃ H Cl Cl Cl 173.0-174.0

TABLE 38

No. X¹ R² Y¹ Y³ Y⁴ m. p. (° C.) 35-001 CF₃ CH₃ Cl H H *1

TABLE 39

No. X¹ R² Y¹ Y³ Y⁴ m. p . (° C.) 36-001 CF₃ CH₃ Cl H H 109.0-110.036-002 CF₃ CH₃ Cl Cl H *1

TABLE 40

No. R² Y¹ Y² Y³ Y⁴ A R¹ m. p. (° C.) 37-001 CH₃ Cl H Cl H CH Et *137-002 H Cl H Cl H N CH₃ (HCl) 167.0-168.0 37-003 CH₃ Cl H Cl H N CH₃ *137-004 CH₃ (S) Cl H Cl H N CH₃ (HCl) 203.0-204.0 95% e. e. [α]_(D)^(18.1) − 5.50° (CHCl₃, c = 0.10) 37-005 H Cl H Cl H N Et *1 37-006 CH₃(S) Cl H Cl H N Et (HCl) 209.0-210.0 95% e. e. [α]_(D) ^(18.5) − 10.90°(CHCl₃, c = 0.10) 37-007 H Cl H Cl H N n-Pr (HCl) 140.0-141.0 37-008 HCl H Cl H N i-Pr *1 37-009 CH₃ Cl H Cl H N i-Pr (HCl) *1 37-010 CH₃ (S)Cl H Cl H N i-Pr (HCl) 215.0-216.0 95% e. e. [α]_(D) ^(18.6) − 15.50°(CHCl₃, c = 0.10) 37-011 H Cl H Cl H N CH₂Pr-c *1 37-012 H Cl H Cl H Ns-Bu (HCl) 165.0-166.0 37-013 H Cl H Cl H N t-Bu (HCl) 178.0-179.037-014 H Cl H Cl H N CH₂CF₃ (HCl) 141.0-143.0 37-015 H Cl H Cl H NCH(CH₃) Ph *1 37-016 H Cl H Cl H N CH(CH₃) *1 (Ph-4-F) (HCl) 37-017 H ClH CF₃ H N Et *1 37-018 H Cl H CF₃ H N CH₂Pr-c (E) *1 37-019 H Cl HCH₂OCH₃ H N i-Pr *1 37-020 H Cl H OCH₃ H N i-Pr *1 37-021 H Cl H OCH₂CF₃H N CH₃ *1 37-022 H Br H Br H N i-Pr (HCl) 160.0-180.0 37-023 H Br H BrH N CH₂CF₃ (HCl) 165.0-175.0 37-024 CH₃ (S) Cl H Cl H N n-Pr (HCl) *183% e. e. [α]_(D) ^(25.4) − 6.66° (CHCl₃, c = 0.10) 37-025 H Cl H CF₃ HN CH₃ *1 37-026 H Cl H CF₃ H N n-Pr *1 37-027 H Cl H CF₃ H N i-Pr *1

In the Tables, the expression “(HCl)” in the column substituent R¹ meansthe compound being a hydrochloride.

TABLE 41

No. R² Y¹ Y² Y³ Y⁴ A R¹ m. p. (° C.) 38-001 H Cl H Cl H CH CH₃ 82.0-85.038-002 H Cl H Cl H N H 138.0-141.0 38-003 CH₃ Cl H Cl H N CH₃ *1 38-004Et Cl H Cl H N CH₃ *1 38-005 H Cl H Cl H N Et 99.0-101.0 38-006 H Cl HCl H N n-Pr *1 38-007 H Cl H Cl H N t-Bu *1 38-008 H Cl H CF₃ H N H *138-009 CH₃ Cl H CF₃ H N H *1 38-010 H Cl H CF₃ H N Et *1 38-011 H Cl HCF₃ H N CH₂Pr-c (E) *1 38-012 H Cl H CH₂OCH₃ H N H *1 38-013 H Cl HCH₂OCH₃ H N i-Pr *1 38-014 H Cl H OCH₃ H N H *1 38-015 H Cl H OCH₃ H NCH₃ *1 38-016 H Cl H OCH₃ H N i-Pr *1

TABLE 42

No. R² Y¹ Y² Y³ Y⁴ A m. p. (° C.) 39-001 CH₃ F H H H CF 111.0-112.039-002 CH₃ F H H F CH 104.0-105.0 39-003 CH₃ F H F H CH 116.0-117.039-004 CH₃ F H Cl H CH 73.0-74.0 39-005 CH₃ F H CF₃ H CH 108.0-109.039-006 CH₃ Cl H Cl H CH 120.0-121.0 39-007 H Cl H Cl H N *1 39-008 CH₃Cl H Cl H N *1 39-009 H Cl H CF₃ H N *1 39-010 CH₃ Cl H CF₃ H N *139-011 H Cl H CH₂OCH₃ H N *1 39-012 H Cl H OCH₃ H N *1

TABLE 43

No. R² Y¹ Y² Y³ Y⁴ A m. p. (° C.) 40-001 CH₃ Cl H Cl H N *1 40-002 CH₃Cl H CF₃ H N *1

TABLE 44

No. R² Y¹ Y² Y³ Y⁴ A R¹ m. p. (° C.) 41-001 CH₃ Cl H Cl H CH H *1 41-002H Cl H Cl H N H *1 41-003 CH₃ (S) Cl H Cl H N H 51.0-53.0 95% e. e.[α]_(D) ^(17.8) − 27.40° (CHCl₃, c = 0.10) 41-004 H Cl H Cl H N CH₃ *141-005 CH₃ (S) Cl H Cl H N CH₃ *1 95% e. e. [α]_(D) ^(17.8) − 33. 00°(CHCl₃, c = 0.10) 41-006 CH₃ Cl H Cl H CH Et 90.0-92.0 41-007 CH₃ (S) ClH Cl H N Et *1 95% e. e. [α]_(D) ^(17.9) − 30.00° (CHCl₃, c = 0.10)41-008 t-Bu Cl H Cl H N Et *1 41-009 H Cl H Cl H N n-Pr *1 41-010 H Cl HCl H N i-Pr *1 41-011 CH₃ Cl H Cl H N i-Pr *1 41-012 CH₃ (S) Cl H Cl H Ni-Pr *1 95% e. e. [α]_(D) ^(18.0) − 29.90° (CHCl₃, c = 0.14) 41-013 H ClH Cl H N CH₂Pr-c *1 41-014 H Cl H Cl H N s-Bu *1 41-015 H Cl H Cl H Nt-Bu *1 41-016 H Cl H Cl H N CH₂CF₃ *1 41-017 H Cl H Cl H N CH (CH₃) Ph*1 41-018 H Cl H Cl H N CH (CH₃) *1 (Ph-4-F) 41-019 CH₃ (S) Cl H Cl H Nn-Pr *1 83% e. e. [α]_(D) ^(26.3) − 23.50° (CHCl₃, c = 0.10)

TABLE 45

No. R² Y¹ Y² Y³ Y⁴ A m. p. (° C.) 42-001 CH₃ Cl H Cl H CH *1 42-002 H ClH Cl H N 82.0-84.0 42-003 CH₃ Cl H Cl H N 111.0-112.0 42-004 CH₃ (S) ClH Cl H N *1 95% e. e. [α]_(D) ^(17.5) − 20.20° (CHCl₃, c = 0. 10) 42-005t-Bu Cl H Cl H N *1 42-006 H Br H Br H N *1

Among the compounds shown in Tables 4 to 45, ¹H NMR data of compounds ofwhich melting points are not disclosed in the Tables are shown in Table46.

TABLE 46 No. ¹H NMR (CDCl₃, Me₄Si, 300 MHz) 1-002 δ 7.05-7.75 (m, 13H),5.45-5.55 and 5.1-5.2 (m, 1H), 5.13 and 5.02 (s, 2H), 1.53 and 1.36 (d,J = 7.2 Hz, 3H). 1-003 δ 7.05-7.75 (m, 7H), 6.48 and 6.34 (bs, 1H), 4.61and 4.43 (d, J = 6.3 Hz, 2H), 4.02 and 3.85 (s, 3H). 1-005 δ 7.1-7.9 (m,7H), 6.72 and 6.64 (d, J = 6.9 Hz, 1H), 5.31 and 5.05 (dq, J = 6.9 and6.6 Hz, 1H), 3.96 and 3.83 (s, 3H), 1.59 and 1.45 (d, J = 6.6 Hz, 3H).1-006 δ 7.1-7.75 (m, 7H), 6.84 and 6.69 (d, J = 7.2 Hz, 1H), 5.2-5.35and 4.95-5.1 (m, 1H), 4.35-4.5 and 4.25-4.35 (m, 1H), 1.58 and 1.43 (d,J = 6.9 Hz, 3H), 1.1-1.5 (m, 6H). 1-007 δ 7.15-7.75 (m, 7H), 6.48 and6.45 (bs, 1H), 5.3-5.45 and 5.0-5.25 (m, 1H), 4.54 and 4.38 (q, J = 8.4Hz, 2H), 1.63 and 1.46 (d, J = 6.9 Hz, 3H). 1-008 δ 7.1-7.75 (m, 11H),6.60 and 6.50 (d, J = 7.5 Hz, 1H), 5.25-5.4 and 4.95-5.1 (m, 1H), 5.16and 5.01 (s, 2H), 1.56 and 1.42 (d, J = 6.9 Hz, 3H). 1-009 δ 7.45-7.75(m, 4H), 7.7-7.1 (m, 1H), 6.96 (bs, 1H), 6.7-6.8 (m, 2H), 5.25-5.4 and4.85-5.0 (m, 1H), 4.45-4.65 (m, 1H), 4.35-4.45 and 4.2-4.35 (m, 1H),2.36 and 2.19 (s, 3H), 1.1-1.4 (m, 15H). 1-010 δ 6.6-7.75 (m, 12H),5.3-5.4 and 4.9-5.05 (m, 1H), 5.12 and 4.99 (s, 2H), 4.5-4.65 (m, 1H),2.25 and 2.15 (s, 3H), 1.25-1.55 (m, 9H). 1-013 δ 6.8-7.75 (m, 9H),5.5-5.65 and 5.15-5.25 (m, 1H), 4.0-4.25 (m, 2H), 1.58 and 1.39 (d, J =7.2 Hz, 3H), 1.34 and 1.33 (s, 9H), 1.1-1.3 (m, 3H). 1-020 δ 6.8-7.75(m, 14H), 5.45-5.6 and 5.1-5.25 (m, 1H), 4.15-4.25 and 4.05-4.15 (m,2H), 1.58 and 1.40 (d, J = 7.2 Hz, 3H), 1.28 and 1.23 (t, J = 7.2 Hz,3H). 1-022 δ 8.36 and 8.30 (d, J = 2.1 Hz, 1H), 6.5-7.75 (m, 16H),5.0-5.6 (m, 3H), 1.54 and 1.38 (d, J = 7.2 Hz, 3H). 1-023 δ 6.8-7.8 (m,14H), 5.55-5.7 and 5.15-5.3 (m, 1H), 4.2-4.3 and 4.05-4.2 (m, 2H), 1.61and 1.43 (d, J = 7.2 Hz, 3H), 1.30 and 1.25 (t, J = 7.2 Hz, 3H). 1-024 δ6.85-7.85 (m, 14H), 5.55-5.7 and 5.2-5.35 (m, 1H), 4.4-4.5 and 4.25-4.4(m, 1H), 1.15-1.65 (m, 9H). 1-025 δ 3.6-7.85 (m, 14H), 5.55-5.7 and5.2-5.3 (m, 1H), 3.8-4.05 (m, 2H), 1.63 and 1.43 (d, J = 6.9 Hz, 3H),1.0-1.25 (m, 1H), 0.4-0.55 (m, 2H), 0.15-0.3 (m, 2H). 1-027 δ 8.38 and8.32 (d, J = 2.1 Hz, 1H), 7.2-7.8 (m, 15H), 6.58 and 6.19 (bs, 1H),5.05-5.7 (m, 3H), 1.57 and 1.40 (d, J = 6.9 Hz, 3H). 1-034 δ 6.4-7.8 (m,13H), 4.85-5.55 (m, 2H), 1.2-1.7 (m, 6H). 1-035 δ 7.45-8.1 (m, 7H), 6.70and 6.64 b(bs, 1H), 5.35-5.55 and 5.1-5.25 (m, 1H), 4.2-4.3 and 4.05-4.2(m, 2H), 1.59 and 1.41 (d, J = 6.9 Hz, 3H), 1.30 and 1.22 (t, J = 7.2Hz, 3H). 1-036 δ 6.8-7.75 (m, 9H), 5.45-5.6 and 5.1-5.2 (m, 1H), 4.5-4.7(m, 1H), 4.0-4.3 (m, 2H), 1.1-1.6 (m, 12H). 1-037 δ 6.85-8.25 (m, 12H),4.8-5.65 (m, 1H), 3.95-4.35 (m, 2H), 1.1-1.65 (m, 6H). 1-038 δ 6.4-8.25(m, 12H), 4.85-5.85 (m, 1H), 4.3-4.65 (m, 2H), 1.15-1.7 (m, 3H). 1-039 δ6.6-8.45 (m, 15H), 4.8-5, 8 (m, 3H), 1.5-1.65 (m, 3H). 1-041 δ 6.6-7.75(m, 8H), 5.35-5.5 and 5.0-5.15 (m, 1H), 3.95-4.05 and 3.8-3.9 (m, 2H),1.6-1.65 and 1.4-1.45 (m, 3H), 0.95-1.3 (m, 1H), 0.45-0.55 (m, 2H),0.15-0.3 (m, 2H). 1-042 δ 6.4-7.75 (m, 7H), 5.3-5.45 and 5.0-5.15 (m,1H), 4.00 and 3.87 (d, J = 6.9 Hz, 2H), 1.75 and 1.43 (d, J = 6.9 Hz,3H), 1.0-1.3 (m, 1H), 0.45-0.6 (m, 2H), 0.15-0.3 (m, 2H). 1-043 δ7.1-7.75 (m, 7H), 6.66 and 6.55 (bs, 1H), 5.35-5.5 and 5.0-5.15 (m, 1H),4.25 and 4.10 (q, J = 7.2 Hz, 2H), 1.60 and 1.21 (d, J = 6.6 Hz, 3H),1.32 and 1.19 (t, J = 7.2 Hz, 3H). 1-044 δ 7.1-7.75 (m, 7H), 6.69 and6.61 (bs, 1H), 5.35-5.5 and 5.0-5.15 (m, 1H), 4.25-4.5 (m, 1H), 1.1-1.65(m, 9H). 1-045 δ 7.1-7.75 (m, 7H), 6.64 and 6.53 (bs, 1H), 5.35-5.5 and5.0-5.15 (m, 1H), 4.25 and 4.10 (q, J = 7.2 Hz, 2H), 1.55-1.65 and1.35-1.45 (m, 3H), 1.31 and 1.19 (t, J = 7.2 Hz, 3H). 1-046 δ 7.1-7.75(m, 7H), 6.67 and 6.59 (bs, 1H), 5.3-5.5 and 5.0-5.15 (m, 1H), 4.25-4.5(m, 1H), 1.1-1.65 (m, 9H). 1-047 δ 7.15-7.75 (m, 7H), 6.71 and 6.64 (bs,1H), 5.35-5.5 and 5.0-5.15 (m, 1H), 3.95-4.05 and 3.8-3.9 (m, 2H),1.6-1.65 and 1.4-1.45 (m, 3H), 0.95-1.3 (m, 1H), 0.4-0.55 (m, 2H),0.15-0.3 (m, 2H). 1-048 δ 7.05-7.75 (m, 7H), 6.42 and 6.28 (bs, 1H),5.35-5.5 and 5.05-5.2 (m, 1H), 4.5-4.65 and 4.3-4.45 (m, 2H), 1.6-1.65and 1.4-1.45 (m, 3H). 1-049 δ 6.95-7.75 (m, 6H), 6.55 (bs, 1H), 5.3-5.45and 5.0-5.1 (m, 1H), 4.2-4.3 and 4.05-4.2 (m, 2H), 1.15-1.65 (m, 6H).1-050 δ 7.0-7.75 (m, 7H), 6.47 and 6.59 (bs, 1H), 5.35-5.5 and 5.05-5.15(m, 1H), 4.05-4.35 (m, 2H), 1.6-1.65 and 1.4-1.45 (m, 3H), 1.33 and 1.19(t, J = 7.2 Hz, 3H). 1-051 δ 6.95-7.75 (m, 6H), 6.56 and 6.47 (bs, 1H),5.3-5.45 and 5.0-5.15 (m, 1H), 4.01 and 3.85 (s, 3H), 1.55-1.65 and1.4-1.45 (m, 3H). 1-052 δ 6.95-7.75 (m, 6H), 6.5-6.7 (m, 1H), 5.3-5.45and 5.0-5.15 (m, 1H), 4.2-4.35 and 4.05-4.2 (m, 2H), 1.6-1.65 and1.4-1.5 (m, 3H), 1.33 and 1.21 (t, J = 7.2 Hz, 3H). 1-053 δ 6.6-7.75 (m,8H), 5.25-5.4 and 5.0-5.15 (m, 1H), 4.05-4.3 (m, 2H), 1.61 and 1.46 (d,J = 6.9 Hz, 3H), 1.31 and 1.19 (t, J = 7.2 Hz, 3H). 1-054 δ 7.2-7.75 (m,7H), 6.77 and 6.64 (bs, 1H), 5.25-5.4 and 5.0-5.1 (m, 1H), 4.24 and 4.09(q, J = 7.2 Hz, 2H), 1.59 and 1.46 (d, J = 6.9 Hz, 3H), 1.31 and 1.19(t, J = 7.2 Hz, 3H). 1-055 δ 7.1-7.75 (m, 12H), 6.49 (bs, 1H), 4.85-5.45(m, 2H), 1.35-1.7 (m, 6H). 1-057 δ 6.95-7.75 (m, 7H), 6.80 and 6.69 (bs,1H), 5.25-5.4 and 4.95-5.1 (m, 1H), 4.0-4.3 (m, 2H), 1.60 and 1.45 (d, J= 7.2 Hz, 3H), 1.15-1.35 (m, 3H). 1-058 δ 7.15-7.75 (m, 7H), 6.78 and6.66 (bs, 1H), 5.25-5.35 and 4.95-5.1 (m, 1H), 4.0-4.3 (m, 2H),1.55-1.65 and 1.4-1.5 (m, 3H), 1.15-1.35 (m, 3H). 1-060 δ 7.15-7.8 (m,7H), 6.62 (bs, 1H), 5.15-5.3 and 4.95-5.15 (m, 1H), 4.05-4.35 (m, 2H),3.45-3.65 (m, 2H), 3.28 and 2.96 (s, 3H), 1.61 and 1.45 (d, J = 6.9 Hz,3H). 1-061 δ 7.15-7.75 (m, 11H), 6.41 (bs, 1H), 5.0-5.5 (m, 3H), 1.60and 1.43 (d, J = 6.9 Hz, 3H). 1-062 δ 7.1-7.75 (m, 7H), 6.3-6.75 (m,3H), 4.95-5.35 (m, 3H), 1.56 and 1.43 (d, J = 6.9 Hz, 3H). 1-063 δ 8.38and 8.28 (d, J = 2.1 Hz, 1H), 7.15-7.75 (m, 9H), 6.41 (bs, 1H), 5.0-5.45(m, 3H), 1.57 and 1.42 (d, J = 7.2 Hz, 3H). 1-064 δ 8.25-8.45 (m, 1H),7.05-7.75 (m, 9H), 6.3-6.45 (m, 1H), 5.0-5.55 (m, 3H), 1.64 and 1.44 (d,J = 6.9 Hz, 3H). 1-065 δ 7.05-7.75 (m, 7H), 6.78 and 6.66 (bs, 1H),5.2-5.45 and 4.95-5.1 (m, 1H), 4.0-4.3 (m, 2H), 1.4-1.65 (m, 3H),1.15-1.35 (m, 3H). 1-066 δ 7.05-7.75 (m, 7H), 6.82 and 6.68 (bs, 1H),5.2-5.45 and 4.95-5.1 (m, 1H), 4.2-4.5 (m, 1H), 1.1-1.65 (m, 9H). 1-067δ 7.05-7.8 (m, 7H), 6.68 and 6.67 (bs, 1H), 4.95-5.45 (m, 1H), 3.98 and3.85 (d, J = 7.2 Hz, 2H), 1.61 and 1.45 (d, J = 7.2 Hz, 3H), 0.95-1.2(m, 1H), 0.4-0.55 (m, 2H), 0.15-0.25 (m, 2H). 1-068 δ 7.1-7.8 (m, 7H),6.46 (bs, 1H), 5.3-5.45 and 5.0-5.2 (m, 1H), 4.45-4.6 and 4.3-4.45 (m,2H), 1.63 and 1.46 (d, J = 6.9 Hz, 3H). 1-069 δ 8.25-8.4 (m, 1H),6.4-7.75 (m, 10H), 5.0-5.45 (m, 3H), 1.56 and 1.42 (d, J = 6.9 Hz, 3H).1-070 δ 7.05-7.75 (m, 7H), 6.72 (bs, 1H), 5.3-5.45 and 4.95-5.1 (m, 1H),3.97 and 3.83 (s, 3H), 2.36 and 2.35 (s, 3H), 1.4-1.6 (m, 3H). 1-071 δ7.05-7.75 (m, 7H), 6.7-6.85 (m, 1H), 5.3-5.45 and 4.95-5.1 (m, 1H),4.0-4.3 (m, 2H), 2.36 and 2.35 (s, 3H), 1.58 and 1.44 (d, J = 6.9 Hz,3H), 1.15-1.35 (m, 3H). 1-072 δ 6.5-8.0 (m, 8H), 5.25-5.4 and 5.0-5.15(m, 1H), 4.2-4.3 and 4.0-4.2 (m, 2H), 1.63 and 1.47 (d, J = 6.9 Hz, 3H),1.15-1.35 (m, 3H). 1-073 δ 6.65-7.75 (m, 8H), 5.25-5.4 and 5.0-5.1 (m,1H), 3.75-4.0 (m, 6H), 1.57 and 1.43 (d, J = 6.9 Hz, 3H). 1-074 δ6.7-7.75 (m, 8H), 5.25-5.4 and 4.95-5.1 (m, 1H), 4.0-4.3 (m, 2H), 3.82and 3.81 (s, 3H), 1.58 and 1.43 (d, J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H).1-075 δ 7.0-7.75 (m, 7H), 6.6-6.9 (m, 1H), 5.25-5.4 and 4.95-5.1 (m,1H), 4.15-4.3 and 4.0-4.15 (m, 2H), 2.50 and 2.48 (s, 3H), 1.4-1.65 (m,3H), 1.15-1.35 (m, 3H). 1-076 δ 7.3-7.8 (m, 7H), 6.59 (bs, 1H), 5.2-5.4and 5.0-5.2 (m, 1H), 4.05-4.3 (m, 2H), 2.7-2.8 (m, 3H), 1.45-1.7 (m,3H), 1.15-1.35 (m, 3H). 1-077 δ 7.3-8.05 (m, 7H), 6.72 and 6.55 (bs,1H), 5.25-5.35 and 5.0-5.15 (m, 1H), 4.26 and 4.10 (q, J = 7.2 Hz, 2H),3.11 and 3.06 (s, 3H), 1.65 and 1.48 (d, J = 6.9 Hz, 3H), 1.32 and 1.19(t, J = 7.2 Hz, 3H). 1-078 δ 7.3-8.05 (m, 7H), 6.65 (bs, 1H), 5.25-5.4and 5.0-5.2 (m, 1H), 4.25 and 4.09 (q, J = 7.2 Hz, 2H), 2.62 and 2.61(s, 3H), 1.63 and 1.47 (d, J = 6.9 Hz, 3H), 1.32 and 1.18 (t, J = 7.2Hz, 3H). 1-079 δ 7.2-7.8 (m, 7H), 6.65-6.85 (m, 1H), 5.3-5.45 and5.0-5.15 (m, 1H), 3.95-4.3 (m, 5H), 2.15-2.25 (m, 3H), 1.60 and 1.45 (d,J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-080 δ 7.2-7.75 (m, 7H), 6.45-6.75(m, 1H), 5.2-5.35 and 5.0-5.15 (m, 1H), 4.01 and 3.84 (s, 3H), 1.63 and1.47 (d, J = 6.9 Hz, 3H). 1-081 δ 7.2-7.75 (m, 7H), 6.75 and 6.55 (bs,1H), 5.2-5.35 and 5.0-5.15 (m, 1H), 4.05-4.3 (m, 2H), 1.63 and 1.47 (d,J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-083 δ 7.15-7.75 (m, 7H), 6.6-6.8(m, 2H), 5.7-5.85 (m, 1H), 5.0-5.4 (m, 2H), 3.99 and 3.84 (s, 3H), 1.59and 1.45 (d, J = 7.2 Hz, 3H). 1-084 δ 7.15-7.75 (m, 7H), 6.55-6.85 (m,2H), 5.7-5.85 (m, 1H), 5.0-5.4 (m, 2H), 4.15-4.3 and 4.0-4.15 (m, 2H),1.60 and 1.45 (d, J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-085 δ 7.25-7.75(m, 12H), 6.72 (bs, 1H), 5.35-5.45 and 5.05-5.2 (m, 1H), 4.00 and 3.87(s, 3H), 1.63 and 1.49 (d, J = 6.9 Hz, 3H). 1-086 δ 7.25-7.75 (m, 12H),6.7-6.85 (m, 1H), 5.35-5.5 and 5.05-5.2 (m, 1H), 4.0-4.3 (m, 2H), 1.64and 1.49 (d, J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-087 δ 7.25-7.75 (m,11H), 6.65-6.8 (m, 1H), 5.35-5.45 and 5.05-5.2 (m, 1H), 4.01 and 3.87(s, 3H), 1.63 and 1.49 (d, J = 6.9 Hz, 3H). 1-088 δ 7.25-7.75 (m, 11H),6.73 (bs, 1H), 5.3-5.45 and 5.05-5.2 (m, 1H), 4.0-4.3 (m, 2H), 1.64 and1, 49 (d, J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-089 δ 7.2-7.75 (m, 7H),7.1-7.65 (m, 2H), 6.6-6.9 (m, 1H), 6.3-6.4 (m, 2H), 5.3-5.45 and5.0-5.15 (m, 1H), 4.0-4.3 (m, 2H), 1.62 and 1.48 (d, J = 6.9 Hz, 3H),1.15-1.35 (m, 3H). 1-090 δ 7.25-7.95 (m, 10H), 6.4-6.8 (m, 1H),5.25-5.45 and 5.0-5.2 (m, 1H), 4.05-4.3 (m, 2H), 1.62 and 1.47 (d, J =6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-091 δ 7.2-8.0 (m, 8H), 6.6-6.85 (m,2H), 5.25-5.4 and 5.0-5.2 (m, 1H), 4.05-4.3 (m, 2H), 1.63 and 1.48 (d, J= 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-092 δ 7.0-7.75 (m, 7H), 6.70 (bs,1H), 5.25-5.4 and 5.0-5.15 (m, 1H), 4.05-4.3 (m, 2H), 1.61 and 1.45 (d,J = 6.9 Hz, 3H), 1.15-1.35 (m, 3H). 1-093 δ 6.6-7.75 (m, 8H), 5.25-5.4and 5.0-5.15 (m, 1H), 4.05-4.3 (m, 2H), 1.15-1.65 (m, 6H). 1-094 δ6.9-7.75 (m, 7H), 6.61 (bs, 1H), 5.0-5.3 (m, 1H), 4.15-4.35 (m, 2H),3.5-3.6 (m, 2H), 3.29 and 2.96 (s, 3H), 1.4-1.85 (m, 3H). 1-095 δ6.4-7.75 (m, 7H), 5.3-5.5 and 5.0-5.1 (m, 1H), 4.2-4.35 and 4.05-4.2 (m,2H), 1.4-1.65 (m, 3H), 1.15-1.4 (m, 3H). 1-096 δ 7.15-7.8 (m, 7H), 7.10and 6.81 (bs, 1H), 5.2-5.4 and 4.9-5.05 (m, 1H), 4.20 and 4.07 (q, J =6.9 Hz, 2H), 3.38 and 2.23 (s, 3H), 1.35-1.6 (m, 3H), 1.29 and 1.18 (t,J = 6.9 Hz, 3H). 1-097 δ 7.0-8.05 (m, 7H), 6.91 (bs, 1H), 5.2-5.4 and4.85-5.05 (m, 1H), 4.19 and 4.06 (q, J = 7.0 Hz, 2H), 2.35 and 2.34 (s,3H), 2.32 and 2.21 (s, 3H), 1.52 and 1.38 (d, J = 7.2 Hz, 3H), 1.28 and1.18 (t, J = 7.0 Hz, 3H). 1-098 δ 7.4-7.8 (m, 7H), 6.54 (bs, 1H),5.0-5.2 (m, 1H), 4.0-4.3 (m, 2H), 1.1-1.65 (m, 6H). 1-099 δ 6.7-7.8 (m,8H), 5.35-5.5 and 5.0-5.15 (m, 1H), 4.0-4.25 (m, 2H), 3.75-3.35 (m, 3H),1.15-1.6 (m, 6H). 1-100 δ 6.7-8.25 (m, 9H), 4.95-5.4 (m, 1H), 4.0-4.3(m, 4H), 1.0-1.6 (m, 9H). 1-101 δ 6.7-8.0 (m, 8H), 5.0-5.85 (m, 2H),3.45-4.35 (m, 6H), 1.15-1.7 (m, 6H). 1-102 δ 6.65-8.35 (m, 11H),5.5-5.65 and 5.05-5.2 (m, 1H), 4.0-4.35 (m, 2H), 1.05-1.65 (m, 6H).2-006 δ 8.49 and 8.44 (d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J = 2.1 Hz,1H), 7.35-7.75 (m, 4H), 6.48 (bs, 1H), 4.75 and 4.52 (d, J = 6.0 Hz,2H), 4.26 and 4.07 (t, J = 6.9 Hz, 2H), 1.65-1.8 and 1.5-1.65 (m, 2H),1.35-1.5 and 1.2-1.35 (m, 2H), 0.93 and 0.89 (t, J = 7.2 Hz, 3H). 2-007δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J = 2.1 Hz, 1H),7.35-7.75 (m, 4H), 6.48 (bs, 1H), 4.77 and 4.53 (d, J = 5.7 Hz, 2H),4.02 and 3.85 (d, J = 6.9 Hz, 2H), 1.85-2.15 (m, 1H), 0.96 and 0.83 (d,J = 6.9 Hz, 6H). 2-008 δ 8.50 and 8.45 (bs, 1H), 7.75-7.85 (m, 1H),7.35-7.7 (m, 4H), 6.59 (bs, 1H), 4.78 and 4.53 (d, J = 6.0 Hz, 2H), 4.07and 3.89 (d, J = 7.2 Hz, 2H), 1.0-1.25 (m, 1H), 0.4-0.6 (m, 2H),0.15-0.35 (m, 2H). 2-010 δ 8.51 and 8.44 (d, J = 2.1 Hz, 1H), 7.80 and7.79 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.49 (bs, 1H), 4.75-4.9 and4.6-4.75 (m, 1H), 4.77 and 4.53 (d, J = 6.0 Hz, 2H), 1.95-2.4 (m, 4H),1.5-1.85 (m, 2H). 2-012 δ 8.49 and 8.44 (d, J = 2.1 Hz, 1H), 7.80 and7.79 (d, J = 2.1 Hz, 1H), 7.3-7.75 (m, 4H), 6.45-6.6 (m, 1H), 5.8-6.1(m, 1H), 5.1-5.4 (m, 2H), 4.7-4.8 (m, 2H), 4.5-4.6 (m, 2H). 2-013 δ 8.50and 8.43 (d, J = 2.1 Hz, 1H), 7.79 and 7.77 (d, J = 2.1 Hz, 1H),7.15-7.75 (m, 8H), 6.39 (bs, 1H), 5.24 and 5.06 (s, 2H), 4.77 and 4.52(d, J = 6.3 Hz, 2H). 2-014 δ 8.80 and 8.75 (s, 1H), 8.03 and 8.01 (s,1H), 7.35-7.75 (m, 4H), 6.44 (bs, 1H), 4.77 and 4.57 (d, J = 5.1 Hz,2H), 4.09 and 3.89 (s, 3H). 2-015 δ 8.79 and 8.70 (s, 1H), 8.02 and 8.00(s, 1H), 7.35-7.75 (m, 4H), 6.85 and 6.70 (bs, 1H), 5.78 and 5.29 (m,1H), 4.07 and 3.88 (s, 3H), 1.59 and 1.48 (d, J = 6.9 Hz, 3H). 2-017 δ8.80 and 8.75 (s, 1H), 8.03 and 8.00 (s, 1H), 7.3-7.75 (m, 4H), 6.46(bs, 1H), 4.79 and 4.57 (d, J = 6.0 Hz, 2H), 4.24 and 4.05 (t, J = 6.9Hz, 2H), 1.7-1.85 and 1.55-1.7 (m, 2H), 0.99 and 0.86 (t, J = 7.5 Hz,3H). 2-021 δ 8.79 and 8.74 (s, 1H), 8.02 and 7.99 (s, 1H), 7.35-7.7 (m,4H), 6.47 (bs, 1H), 4.80 and 4.56 (d, J = 5.1 Hz, 2H), 4.05 and 3.86 (d,J = 6.9 Hz, 2H), 2.09 and 1.93 (m, 1H), 0.96 and 0.83 (d, J = 6.9 Hz,6H). 2-022 δ 8.81 and 8.75 (s, 1H), 8.02 and 8.01 (s, 1H), 7.35-7.75 (m,4H), 6.51 (bs, 1H), 4.81 and 4.57 (d, J = 6.3 Hz, 2H), 4.09 and 3.91 (d,J = 7.2 Hz, 2H), 1.15-1.3 and 1.0-1.15 (m, 1H), 0.5-0.6 and 0.4-0.5 (m,2H), 0.25-0.35 and 0.15-0.25 (m, 2H). 2-025 δ 8.80 and 8.74 (s, 1H),8.03 and 7.99 (s, 1H), 7.35-7.75 (m, 4H), 6.49 (bs, 1H), 4.79 and 4.56(d, J = 6.0 Hz, 2H), 4.33 and 4.17 (m, 1H), 1.45-1.8 (m, 2H), 1.32 and1.18 (d, J = 6.3 Hz, 3H), 0.95 and 0.83 (t, J = 7.5 Hz, 3H). 2-026 δ8.80 and 8.73 (s, 1H), 8.03 and 8.00 (s, 1H), 7.35-7.75 (m, 4H), 6.45(bs, 1H), 4.8-4.9 and 4.6-4.75 (m, 1H), 4.79 and 4.56 (d, J = 6.0 Hz,2H), 1.6-2.4 (m, 6H). 2-027 δ 8.78 and 8.73 (s, 1H), 8.02 and 7.98 (s,1H), 7.35-7.75 (m, 4H), 6.48 (bs, 1H), 4.80 and 4.55 (d, J = 6.3 Hz,2H), 4.1-4.2 and 3.9-4.05 (m, 1H), 1.5-1.5 (m, 4H), 0.95 and 0.83 (t, J= 7.5 Hz, 6H). 2-028 δ 8.81 and 8.75 (s, 1H), 8.02 and 8.00 (s, 1H),7.4-7.75 (m, 4H), 6.45-6.6 (m, 1H), 4.7-4.85 and 4.5-4.6 (m, 2H),3.7-3.8 and 3.55-3.65 (m, 1H), 2.40 and 1.26 (d, J = 6.3 Hz, 3H),0.8-1.15 (m, 1H), 0.2-0.55 (m, 4H). 2-029 δ 8.79 and 8.74 (s, 1H), 8.03and 7.99 (s, 1H), 7.3-7.7 (m, 4H), 6.4-6.55 (m, 1H), 4.85-4.9 and4.7-4.75 (m, 1H), 4.77 and 4.56 (d, J = 6.3 Hz, 2H), 1.5-1.95 (m, 8H).2-030 δ 8.80 and 8.76 (s, 1H), 8.40 and 8.02 (s, 1H), 7.3-7.75 (m, 4H),6.39 (bs, 1H), 6.06 and 5.95 (tt, J = 55.8 and 4.2 Hz, 1H), 4.81 and4.60 (d, J = 5.7 Hz, 2H), 4.44 and 4.25 (td, J = 13.5, 4.2 Hz, 2H).2-031 δ 8.76 (s, 1H), 8.05 (s, 1H), 7.35-7.7 (m, 4H), 6.39 (bs, 1H),6.77 (tt, J = 55.2 and 4.2 Hz, 1H), 4.81 (d, J = 6.3 Hz, 2H), 4.44 (td,J = 13.2, 4.2 Hz, 2H). 2-032 δ 8.81 and 8.76 (s, 1H), 8.04 and 8.03 (s,1H), 7.3-7.75 (m, 4H), 6.34 (bs, 1H), 4.82 and 4.61 (d, J = 6.3 Hz, 2H),4.63 and 4.43 (q, J = 8.7 Hz, 2H). 2-033 δ 8.82 and 8.73 (s, 1H), 8.06and 8.03 (s, 1H), 7.25-7.75 (m, 4H), 6.62 (bs, 1H), 5.82 and 5.36 (m,1H), 4.62 and 4.43 (q, J = 8.7 Hz, 2H), 1.65 and 1.49 (d, J = 6.9 Hz,3H). 2-034 δ 8.80 and 8.77 (s, 1H), 8.03 and 8.01 (s, 1H), 7.35-7.75 (m,4H), 6.44 and 6.80 (bs, 1H), 4.78 and 4.58 (d, J = 6.0 Hz, 2H), 4.42 and4.24 (t, J = 6.6 Hz, 2H), 2.85 and 2.72 (t, J = 6.6 Hz, 2H), 2.06 and2.05 (s, 3H). 2-035 δ 8.80 and 8.75 (s, 1H), 8.03 and 8.00 (s, 1H),7.3-7.75 (m, 4H), 6.44 and 6.54 (bs, 1H), 4.05-5.0 (m, 5H), 2.7-3.15 (m,2H), 1.99 and 1.90 (s, 3H). 2-036 δ 8.82 and 8.76 (s, 1H), 8.07 and 8.03(s, 1H), 7.3-7.75 (m, 4H), 6.39 (bs, 1H), 4.93 and 4.72 (s, 2H), 4.81and 4.64 (d, J = 6.0 Hz, 2H). 2-037 δ 8.83 and 8.75 (s, 1H), 8.07 and8.03 (s, 1H), 7.35-7.75 (m, 4H), 6.41 (bs, 1H), 5.10 and 4.94 (q, J =6.9 Hz, 1H), 4.78 and 4.63 (d, J = 6.0 Hz, 2H), 1.77 and 1.58 (d, J =6.9 Hz, 3H). 2-038 δ 8.81 and 8.77 (s, 1H), 8.05 and 8.03 (s, 1H),7.35-7.75 (m, 4H), 6.44 (bs, 1H), 4.81 and 4.60 (d, J = 6.0 Hz, 2H),4.48 and 4.30 (t, J = 6.3 Hz, 2H), 2.84 and 2.71 (t, J = 6.3 Hz, 2H).2-039 δ 8.83 and 8.72 (s, 1H), 8.10 and 8.06 (s, 1H), 7.35-7.75 (m, 5H),6.44 and 6.32 (bs, 1H) 4.91 and 4.89 (bs, 2H), 4.66 and 4.64 (bs, 2H),3.9-4.05 (m, 2H). 2-040 δ 8.79 and 8.73 (s, 1H), 8.01 and 7.99 (s, 1H),7.3-7.7 (m, 4H), 6.45-6.55 (m, 1H), 5.8-6.2 (m, 1H), 5.15-5.4 (m, 2H),4.80 and 4.57 (d, J = 6.3 Hz, 2H), 4.75-4.8 and 4.55-4.6 (m, 2H). 2-041δ 8.80 and 8.74 (s, 1H), 8.01 (bs, 1H), 7.3-7.75 (m, 4H), 6.43 (bs, 1H),4.85-5.05 (m, 2H), 4.82 and 4.57 (d, J = 6.0 Hz, 2H), 4.70 and 4.50 (s,2H), 1.80 and 1.69 (s, 3H). 2-042 δ 8.81 and 8.74 (s, 1H), 8.02 and 8.00(s, 1H), 7.35-7.75 (m, 4H), 6.45 (bs, 1H), 5.75-6.05 (m, 1H), 5.05-5.35(m, 2H), 4.8-4.9 and 4.65-4.75 (m, 1H), 4.81 and 4.57 (d, J = 6.3 Hz,2H), 1.44 and 1.27 (d, J = 6.6 Hz, 3H). 2-044 δ 8.81 and 8.75 (s, 1H),8.04 and 8.02 (s, 1H), 7.35-7.75 (m, 4H), 6.41 (bs, 1H), 4.87 and 4.68(d, J = 2.7 Hz, 2H), 4.81 and 4.61 (d, J = 6.0 Hz, 2H), 2.51 and 2.46(t, J = 2.7 Hz, 1H). 2-046 δ 8.77 and 8.72 (s, 1H), 7.99 and 7.97 (s,1H), 7.2-7.7 (m, 6H), 6.85-7.15 (m, 2H), 6.48 (bs, 1H), 5.37 and 5.18(s, 2H), 4.78 and 4.55 (d, J = 6.0 Hz, 2H). 2-048 δ 8.77 and 8.71 (s,1H), 8.00 and 7.97 (s, 1H), 7.2-7.7 (m, 6H), 6.95-7.1 (m, 2H), 6.45 (bs,1H), 5.26 and 5.06 (s, 2H), 4.78 and 4.55 (d, J = 6.0 Hz, 2H). 2-050 δ8.80 and 8.72 (s, 1H), 8.00 (bs, 1H), 7.1-7.7 (m, 8H), 6.41 (bs, 1H),5.26 and 5.07 (s, 2H), 4.80 and 4.56 (d, J = 6.0 Hz, 2H). 2-051 δ 8.79and 8.73 (s, 1H), 8.01 and 7.99 (s, 1H), 7.2-7.7 (m, 8H), 6.41 (bs, 1H),5.26 and 5.07 (s, 2H), 4.80 and 4.56 (d, J = 6.0 Hz, 2H). 2-053 δ 8.77and 8.72 (s, 1H), 8.00 and 7.97 (s, 1H), 7.05-7.7 (m, 8H), 6.4-6.5 (m,1H), 5.26 and 5.08 (s, 2H), 4.78 and 4.55 (d, J = 6.3 Hz, 2H), 2.33 and2.31 (s, 3H). 2-054 δ 8.76 and 8.71 (s, 1H), 7.99 and 7.96 (s, 1H),7.05-7.7 (m, 8H), 6.4-6.5 (m, 1H), 5.25 and 5.07 (s, 2H), 4.77 and 4.54(d, J = 6.3 Hz, 2H), 2.34 and 2.32 (s, 3H). 2-055 δ 8.78 and 8.73 (s,1H), 8.00 and 7.98 (s, 1H), 7.15-7.75 (m, 8H), 6.4-6.5 (m, 1H), 5.27 and5.10 (s, 2H), 4.79 and 4.57 (d, J = 6.0 Hz, 2H), 1.32 and 1.30 (s, 9H).2-056 δ 8.81 and 8.73 (s, 1H), 8.00 (bs, 1H), 7.25-7.7 (m, 8H). 6.45(bs, 1H), 5.51 and 5.33 (s, 2H), 4.83 and 4.57 (d, J = 6.0 Hz, 2H).2-057 δ 8.79 and 8.72 (s, 1H), 8.00 and 7.99 (s, 1H), 7.25-7.7 (m, 8H),6.43 (bs, 1H), 5.34 and 5.15 (s, 2H), 4.81 and 4.55 (d, J = 6.0 Hz, 2H).2-058 δ 8.80 and 8.72 (s, 1H), 8.00 (bs, 1H), 7.25-7.7 (m, 8H), 6.40(bs, 1H), 5.35 and 5.16 (s, 2H), 4.83 and 4.56 (d, J = 6.0 Hz, 2H).2-059 δ 8.78 and 8.72 (s, 1H), 8.00 and 7.98 (s, 1H), 7.2-7.7 (m, 5H),6.75-7.0 (m, 3H), 6.44 (bs, 1H), 5.28 and 5.09 (s, 2H), 4.80 and 4.56(d, J = 6.0 Hz, 2H), 3.79 and 3.76 (s, 3H). 2-060 δ 8.78 and 8.74 (s,1H), 8.01 and 7.97 (s, 1H), 7.2-7.75 (m, 6H), 6.8-6.95 (m, 2H), 6.4-6.5(m, 1H), 5.24 and 5.05 (s, 2H), 4.77 and 4.56 (d, J = 6, 0 Hz, 2H), 3.81and 3.79 (s, 3H). 2-061 δ 8.79 and 8.73 (s, 1H), 7.99 (bs, 1H), 7.15-7.7(m, 8H), 6.45 (bs, 1H), 5.39 and 5.21 (s, 2H), 4.80 and 4.56 (d, J = 6.3Hz, 2H). 2-062 δ 8.81 and 8.73 (s, 1H), 8.00 (bs, 1H), 7.1-7.7 (m, 8H),6.39 (bs, 1H), 5.30 and 5.11 (s, 2H), 4.82 and 4.57 (d, J = 6.3 Hz, 2H).2-063 δ 8.79 and 8.72 (s, 1H), 8.01 and 7.99 (s, 1H), 7.1-7.7 (m, 8H),6.40 (bs, 1H), 5.29 and 5.10 (s, 2H), 4.81 and 4.56 (d, J = 6.0 Hz, 2H).2-064 δ 8.82 and 8.72 (s, 1H), 7.25-8.25 (m, 9H), 6.3-6.5 (m, 1H), 5.40and 5.20 (s, 2H), 4.86 and 4.57 (d, J = 6.3 Hz, 2H). 2-065 δ 8.79 and8.72 (s, 1H), 8.00 and 7.97 (s, 1H), 7.3-7.7 (m, 8H), 6.63 and 6.56 (bs,1H), 5.47 and 5.29 (s, 2H), 4.84 and 4.55 (d, J = 5.7 Hz, 2H). 2-066 δ8.81 and 8.72 (s, 1H), 8.01 (bs, 1H), 7.25-7.75 (m, 8H), 6.39 (bs, 1H),5.31 and 5.12 (s, 2H), 4.82 and 4.56 (d, J = 6.3 Hz, 2H). 2-067 δ 8.81and 8.72 (s, 1H), 8.00 (bs, 1H), 7.25-7.7 (m, 8H), 6.43 (bs, 1H), 5.36and 5.15 (s, 2H), 4.84 and 4.56 (d, J = 6.0 Hz, 2H). 2-068 δ 8.80 and8.74 (s, 1H), 8.01 and 7.99 (s, 1H), 7.25-7.7 (m, 13H), 6.41 (bs, 1H),5.35 and 5.16 (s, 2H), 4.82 and 4.58 (d, J = 6.3 Hz, 2H). 2-069 δ 8.78and 8.72 (s, 1H), 8.00 and 7.98 (s, 1H), 7.25-7.75 (m, 5H), 6.6-6.9 (m,2H), 6.43 (bs, 1H), 5.31 and 5.12 (s, 2H), 4.78 and 4.55 (d, J = 6.3 Hz,2H). 2-071 δ 8.80 and 8.73 (s, 1H), 8.01 and 8.00 (s, 1H), 6.95-7.75 (m,7H), 6.38 (bs, 1H), 5.23 and 5.04 (s, 2H), 4.80 and 4.56 (d, J = 6.0 Hz,2H). 2-072 δ 8.82 and 8.73 (s, 1H), 8.02 (bs, 1H), 7.3-7.7 (m, 4H),6.65-7.0 (m, 3H), 6.3-6.45 (m, 1H), 5.26 and 5.06 (s, 2H), 4.83 and 4.57(d, J = 6.0 Hz, 2H). 2-073 δ 8.80 and 8.72 (s, 1H), 8.00 (bs, 1H),7.05-7.7 (m, 7H), 6.3-6.5 (m, 1H), 5.23 and 5.04 (s, 2H), 4.80 and 4.56(d, J = 6.3 Hz, 2H). 2-074 δ 8.80 and 8.72 (s, 1H), 8.01 (bs, 1H),7.25-7.7 (m, 4H), 6.85-7.1 (m, 2H), 6.35-6.5 (m, 1H), 5.20 and 5.00 (s,2H), 4.81 and 4.56 (d, J = 6.0 Hz, 2H). 2-075 δ 8.79 and 8.73 (s, 1H),7.98 (bs, 1H), 7.35-7.9 (m, 1H), 6.40 (bs, 1H), 5.46 and 5.27 (s, 2H),4.81 and 4.56 (d, J = 6.0 Hz, 2H). 2-077 δ 8.83 and 8.76 (s, 1H), 8.52and 8.01 (d, J = 4.5 Hz, 1H), 8.00 and 7.99 (s, 1H), 7.05-7.7 (m, 7H),6.45 (bs, 1H), 5.44 and 5.25 (s, 2H), 4.85 and 4.59 (d, J = 5.4 Hz, 2H).2-078 δ 8.81 and 8.74 (s, 1H), 8.5-8.7 (m, 2H), 8.02 and 8.00 (s, 1H),7.80 and 7.78 (t, J = 2.1 Hz, 1H), 7.25-7.75 (m, 5H), 6.40 (bs, 1H),5.32 and 5.13 (s, 2H), 4.81 and 4.57 (d, J = 6.3 Hz, 2H). 2-079 δ 8.80and 8.72 (s, 1H), 8.41 and 8.31 (s, 1H), 8.01 and 7.99 (s, 1H), 7.77 and7.75 (d, J = 2.4 Hz, 1H), 7.25-7.7 (m, 5H), 6.39 (bs, 1H), 5.28 and 5.09(s, 2H), 4.80 and 4.55 (d, J = 6.3 Hz, 2H). 2-080 δ 8.84 and 8.74 (s,1H), 8.5-8.6 (m, 2H), 8.03 and 8.01 (s, 1H), 7.15-7.7 (m, 6H), 6.47 (bs,1H), 5.33 and 5.12 (s, 2H), 4.88 and 4.58 (d, J = 6.0 Hz, 2H). 2-081 δ8.81 and 8.70 (s, 1H), 8.00 and 7.97 (s, 1H), 7.0-7.7 (m, 9H), 6.42 and6.36 (bs, 1H), 5.41 and 5.25 (q, J = 6.9 Hz, 1H), 4.8-4.9 (m, 1H),4.5-4.55 (m, 1H), 1.67 and 1.47 (d, J = 6.9 Hz, 3H). 2-084 δ 8.21 and8.19 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 7.28 and 7.27 (d, J = 2.1Hz, 1H), 6.54 and 6.47 (bs, 1H), 4.71 and 4.51 (d, J = 6.0 Hz, 2H), 4.06and 3.89 (s, 3H), 3.88 and 3.85 (s, 3H). 2-085 δ 8.44 and 8.39 (d, J =2.1 Hz, 1H), 7.4-7.8 (m, 5H), 6.63 and 6.58 (bs, 1H), 4.83 and 4.60 (d,J = 5.7 Hz, 2H), 4.45-4.65 and 4.35-4.55 (m, 1H), 1.33 and 1.20 (d, J =6.3 Hz, 6H). 2-086 δ 8.48 and 8.43 (d, J = 2.1 Hz, 1H), 7.80 and 7.77(d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.53 and 6.46 (bs, 1H), 4.5-4.9(m, 3H), 1.4-2.0 (m, 8H). 2-087 δ 8.45-8.55 (m, 1H), 7.75-7.85 (m, 1H),7.35-7.75 (m, 4H), 6.59 and 6.46 (bs, 1H), 4.78 and 4.55 (d, J = 5.7 Hz,2H), 4.47 and 4.29 (t, J = 6.0 Hz, 2H), 3.79 and 3.67 (t, J = 6.0 Hz,2H). 2-088 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.81 and 7.79 (d, J =2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.52 (bs, 1H), 5.41 and 5.24 (q, J = 5.1Hz, 1H), 4.5-4.9 (m, 2H), 3.45-3.95 (m, 2H), 1.49 and 1.35 (d, J = 5.1Hz, 3H), 1.19 and 1.16 (t, J = 7.2 Hz, 3H). 2-089 δ 8.51 and 8.43 (d, J= 2.4 Hz, 1H), 7.81 and 7.79 (d, J = 2.4 Hz, 1H), 7.3-7.7 (m, 4H), 6.54and 6.48 (bs, 1H), 5.44 and 5.32 (t, J = 3.6 Hz, 1H), 4.8-4.9 and4.55-4.65 (m, 2H), 3.55-4.0 (m, 2H), 1.4-2.0 (m, 6H). 2-090 δ 8.45-8.55(m, 1H), 7.75-7.85 (m, 1H), 7.4-7.75 (m, 4H), 6.84 and 6.49 (bs, 1H),5.18 and 5.12 (t, J = 4.2 Hz, 1H), 4.76 and 4.55 (d, J = 5.7 Hz, 2H),4.29 and 4.14 (d, J = 4.2 Hz, 2H), 3.7-3.95 (m, 4H). 2-091 δ 8.50 and8.47 (d, J = 2.1 Hz, 1H), 7.81 and 7.79 (d, J = 2.1 Hz, 1H), 7.35-7.75(m, 4H), 6.81 and 6.47 (bs, 1H), 4.75 and 4.54 (d, J = 5.7 Hz, 2H), 4.39and 4.22 (t, J = 6.9 Hz, 2H), 2.83 and 2.71 (t, J = 6.9 Hz, 2H), 2.05and 2.04 (s, 3H). 2-092 δ 8.49 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and7.78 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.50 and 6.43 (bs, 1H),4.74 and 4.52 (d, J = 5.7 Hz, 2H), 4.06 and 3.88 (s, 2H), 0.10 and −0.05(s, 9H). 2-093 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.90 and 7.80 (d, J= 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.58 and 6.45 (bs, 1H), 4.75-5.2 (m,2H), 4.5-4.6 (m, 2H), 3.83, 3.78 and 3.76 (s, 3H), 1.99, 1.92, 1.82 and1.81 (s, 3H). 2-094 δ 8.52 and 8.46 (d, J = 2.1 Hz, 1H), 7.84 and 7.81(d, J = 2.1 Hz, 1H), 7.3-7.75 (m, 4H), 6.41 (bs, 1H), 4.90 and 4.71 (s,2H), 4.79 and 4.60 (d, J = 5.7 Hz, 2H). 2-095 δ 8.52 and 8.48 (d, J =2.1 Hz, 1H), 7.80 (d, J = 2.1 Hz, 1H), 7.4-7.75 (m, 4H), 6.96 and 6.47(bs, 1H), 4.82 and 4.60 (s, 2H), 4.80 and 4.56 (d, J = 5.7 Hz, 2H), 3.74and 3.68 (s, 3H). 2-096 δ 8.49 and 8.44 (d, J = 2.1 Hz, 1H), 7.80 and7.77 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.48 (bs, 1H), 5.98 and5.84 (ddd, J = 17.1, 1.8, 6.6 Hz, 1H), 5.27 and 5.14 (dt, J = 17.1, 1.5Hz, 1H), 5.17 and 5.09 (dt, J = 10.8, 1.5 Hz, 1H), 4.75-4.9 and 4.6-4.75(m, 1H), 4.79 and 4.53 (d, J = 5.1 Hz, 2H), 1.43 and 1.26 (d, J = 6.6Hz, 3H). 2-097 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.75-7.85 (m, 1H),7.35-7.75 (m, 4H), 6.3-6.6 (m, 2H), 4.5-5.05 (m, 4H), 2-098 δ 8.49 and8.44 (d, J = 2.1 Hz, 1H), 7.78 and 7.77 (d, J = 2.1 Hz, 1H), 6.95-7.75(m, 8H), 6.46 (bs, 1H), 5.35 and 5.17 (s, 2H), 4.76 and 4.53 (d, J = 5.7Hz, 2H). 2-099 δ 8.51 and 8.44 (d, J = 2.1 Hz, 1H), 7.79 and 7.78 (d, J= 2.1 Hz, 1H), 6.95-7.75 (m, 8H), 6.41 (bs, 1H), 5.27 and 5.09 (m, 2H),4.79 and 4.53 (d, J = 5.7 Hz, 2H). 2-100 δ 8.50 and 8.44 (d, J = 2.1 Hz,1H), 7.80 and 7.77 (d, J = 2.1 Hz, 1H), 6.9-7.75 (m, 8H), 6.43 (bs, 1H),5.24 and 5.06 (s, 2H), 4.77 and 4.53 (d, J = 5.7 Hz, 2H). 2-101 δ 8.51and 8.45 (d, J = 2.1 Hz, 1H), 7.79 and 7.78 (d, J = 2.1 Hz, 1H),7.15-7.75 (m, 8H), 6.52 and 6.45 (bs, 1H), 5.39 and 5.23 (s, 2H), 4.79and 4.54 (d, J = 5.7 Hz, 2H). 2-102 δ 8.51 and 8.44 (d, J = 2.1 Hz, 1H),7.79 and 7.78 (d, J = 2.1 Hz, 1H), 7.1-7.75 (m, 8H), 6.41 (bs, 1H), 5.24and 5.01 (s, 2H), 4.78 and 4.53 (d, J = 5.7 Hz, 2H). 2-103 δ 8.50 and8.42 (d, J = 2.1 Hz, 1H), 7.79 and 7.78 (d, J = 2.1 Hz, 1H), 7.25-7.7(m, 8H), 6.44 (bs, 1H), 5.31 and 5.13 (s, 2H), 4.76 and 4.53 (d, J = 5.1Hz, 2H). 2-104 δ 8.53 and 8.44 (d, J = 1.8 Hz, 1H), 7.81 and 7.80 (d, J= 1.8 Hz, 1H), 7.3-7.75 (m, 8H), 6.38 (bs, 1H), 5.34 and 5.15 (s, 2H),4.83 and 4.54 (d, J = 5.7 Hz, 2H). 2-105 δ 8.50 and 8.43 (d, J = 2.1 Hz,1H), 7.79 and 7.78 (d, J = 2.1 Hz, 1H), 6.95-7.75 (m, 7H), 6.41 (bs,1H), 5.21 and 5.03 (s, 2H), 4.78 and 4.52 (d, J = 5.7 Hz, 2H). 2-106 δ7.89 and 7.87 (s, 1H), 7.4-7.75 (m, 4H), 6.44 (bs, 1H), 4.72 and 4.52(d, J = 6.0 Hz, 2H), 4.31 and 4.14 (q, J = 7.2 Hz, 2H), 1.35 and 1.22(t, J = 7.2 Hz, 3H). 2-107 δ 7.88 and 7.85 (s, 1H), 7.4-7.75 (m, 4H),6.42 (bs, 1H), 4.71 and 4.52 (d, J = 6.3 Hz, 2H), 4.45-4.55 and 4.3-4.45(m, 1H), 1.32 and 1.19 (d, J = 6.3 Hz, 6H). 2-108 δ 7.88 and 7.87 (s,1H), 7.4-7.75 (m, 4H), 6.44 (bs, 1H), 4.74 and 4.52 (d, J = 5.7 Hz, 2H),4.06 and 3.89 (d, J = 7.2 Hz, 2H), 1.0-1.3 (m, 1H), 0.45-0.65 (m, 2H),0.15-0.35 (m, 2H). 2-109 δ 7.89 and 7.87 (s, 1H), 7.4-7.75 (m, 4H), 6.41and 6.40 (bs, 1H), 5.85-6.1 (m, 1H), 5.15-5.4 (m, 2H), 4.75 and 4.74 (d,J = 6.0 Hz, 2H), 4.58 and 4.34 (d, J = 5.1 Hz, 2H). 2-110 δ 7.87 and7.85 (s, 1H), 7.2-7.75 (m, 6H), 6.95-7.1 (m, 2H), 6.38 and 6.36 (bs,1H), 5.24 and 5.06 (s, 2H), 4.72 and 4.52 (d, J = 6.0 Hz, 2H). 2-111 δ8.47 and 8.42 (d, J = 1.5 Hz, 1H), 7.79 and 7.76 (d, J = 1.5 Hz, 1H),7.3-7.75 (m, 4H), 6.62 (bs, 1H), 4.78 and 4.53 (d, J = 5.4 Hz, 2H),4.45-4.6 and 4.25-4.45 (m, 1H), 4.50 and 4.48 (s, 2H), 3.46 and 3.41 (s,3H), 1.33 and 1.18 (d, J = 6.3 Hz, 6H). 2-112 δ 8.08 and 8.06 (dd, J =3.0, 1.9 Hz, 1H), 7.82 and 7.63 (td, J = 7.3, 3.0 Hz, 1H), 7.25-7.75 (m,4H), 6.25-6.45 (m, 1H), 4.63 and 4.51 (d, J = 6.3 Hz, 2H), 4.51 and 4.40(sep, J = 6.3 Hz, 1H), 1.33 and 1.21 (d, J = 6.3 Hz, 6H). 2-113 δ 8.55and 8.39 (d, J = 1.9 Hz, 1H), 7.4-7.8 (m, 5H), 7.1-7.2 and 6.6-6.7 (m,1H), 6.85-6.9 and 4.8-4.9 (m, 2H), 3.85-4.4 (m, 2H), 1.33 and 1.20 (d, J= 6.9 Hz, 3H). 2-118 δ 8.49 (d, J = 2.1 Hz, 1H), 7.4-7.85 (m, 5H), 6.78(bs, 1H), 5.2-5.3 (m, 1H), 3.86 (s, 3H), 1.45 (d, J = 6.6 Hz, 3H). 2-119δ 8.49 and 8.40 (d, J = 1.8 Hz, 1H), 7.82 and 7.78 (d, J = 1.8 Hz, 1H),7.5-7.7 (m, 4H), 5.15-5.25 (m, 1H), 4.05 and 3.88 (s, 3H), 1.85-2.05 (m,1H), 1.6-1.75 (m, 1H), 1.04 (t, J = 7.5 Hz, 3H). 2-121 δ 8.50 and 8.41(d, J = 1.8 Hz, 1H), 7.82 and 7.79 (d, J = 1.8 Hz, 1H), 7.4-7.75 (m,4H), 6.65-7.05 (m, 1H), 5.75-5.85 and 5.2-5.35 (m, 1H), 4.29 and 4.12(q, J = 6.9 Hz, 2H), 1.56 and 1.44 (d, J = 6.9 Hz, 3H), 1.26 and 1.21(t, J = 6.9 Hz, 3H). 2-123 δ 8.50 (d, J = 2.0 Hz, 1H), 7.79 (d, J = 2.0Hz, 1H), 7.4-7.75 (m, 4H), 6.80 (bs, 1H), 5.25 (dq, J = 7.4, 6.8 Hz,1H), 4.12 (q, J = 7.0 Hz, 2H), 1.45 (d, J = 6.8 Hz, 3H), 1.20 (t, J =7.0 Hz, 3H). 2-125 δ 7.25-8.7 (m, 6H), 5.0-6.8 (m, 1H), 4.1-4.35 (m,2H), 1.15-1.35 (m, 3H), 1.00 and 0.94 (s, 9H). 2-127 δ 8.50 (d, J = 1.9Hz, 1H), 7.79 (d, J = 1.9 Hz, 1H), 7.45-7.75 (m, 4H), 6.81 (bs, 1H),5.15-5.35 (m, 1H), 4.02 (t, J = 6.7 Hz, 2H), 1.5-1.7 (m, 2H), 1.45 (d, J= 6.9 Hz, 3H), 0.85 (t, J = 7.4 Hz, 3H). 2-129 δ 8.49 and 8.40 (d, J =1.8 Hz, 1H), 7.81 and 7.78 (d, J = 1.8 Hz, 1H), 7.4-7.75 (m, 4H),6.7-7.05 (m, 1H), 5.7-5.85 and 5.15-5.3 (m, 1H), 4.4-4.55 and 4.4.3-4.4(m, 1H), 1.56 and 1.43 (d, J = 6.6 Hz, 3H), 1.05-1.35 (m, 6H). 2-131 δ8.49 (d, J = 2.0 Hz, 1H), 7.78 (d, J = 2.0 Hz, 1H), 7.45-7.75 (m, 4H),6.84 (bs, 1H), 5.24 (dq, J = 7.8, 6.8 Hz, 1H), 4.35 (sep, J = 6.3 Hz,1H), 1.44 (d, J = 6.8 Hz, 3H), 1.18 (d, J = 6.3 Hz, 6H). 2-137 δ 8.49(d, J = 2.0 Hz, 1H), 7.78 (d, J = 2.0 Hz, 1H), 7.45-7.75 (m, 4H), 6.83(bs, 1H), 5.15-5.3 (m, 1H), 4.05-4.2 (m, 1H), 1.35-1.7 (m, 2H), 1.44 (d,J = 6.8 Hz, 3H), 1.16 (d, J = 6.5 Hz, 3H), 0.82 (t, J = 7.4 Hz, 3H).2-141 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J = 2.1 Hz,1H), 7.35-7.75 (m, 4H), 6.49 (bs, 1H), 4.75 and 4.53 (d, J = 5.4 Hz,2H), 4.24 and 4.06 (t, J = 6.6 Hz, 2H), 1.15-1.8 (m, 6H), 0.8-0.95 (m,3H). 2-144 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.75-7.85 (m, 1H),7.35-7.75 (m, 4H), 6.54 (bs, 1H), 4.78 and 4.52 (d, J = 5.7 Hz, 2H),4.0-4.2 and 3.9-4.0 (m, 1H), 1.4-1.8 (m, 4H), 0.94 and 0.83 (t, J = 7.5Hz, 6H). 2-146 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J= 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.49 (bs, 1H), 4.75 and 4.53 (d, J =5.7 Hz, 2H), 4.24 and 4.06 (t, J = 6.9 Hz, 2H), 1.15-1.8 (m, 8H),0.8-0.95 (m, 3H). 2-149 δ 8.50 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and7.78 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.47 (bs, 1H), 4.75 and4.52 (d, J = 5.7 Hz, 2H), 4.06 and 3.88 (d, J = 6.6 Hz, 2H), 0.75-1.85(m, 11H). 2-150 δ 8.51 and 8.46 (d, J = 2.1 Hz, 1H), 7.82 and 7.80 (d, J= 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 6.39 (bs, 1H), 6.06 and 5.95 (tt, J =55.5 and 4.5 Hz, 1H), 4.78 and 4.56 (d, J = 5.7 Hz, 2H), 4.41 and 4.24(td, J = 13.2, 4.5 Hz, 2H). 2-151 δ 8.52 (d, J = 2.0 Hz, 1H), 7.82 (d, J= 2.0 Hz, 1H), 7.45-7.8 (m, 4H), 6.60 (bs, 1H), 5.32 (dq, J = 7.8, 6.8Hz, 1H), 4.41 (q, J = 8.5 Hz, 2H), 1.47 (d, J = 6.8 Hz, 3H). 2-152 δ8.50 and 8.48 (d, J = 2.1 Hz, 1H), 7.81 and 7.79 (d, J = 2.1 Hz, 1H),7.4-7.75 (m, 4H), 6.90 and 6.52 (bs, 1H), 4.75 and 4.54 (d, J = 5.7 Hz,2H), 4.38 and 4.23 (t, J = 5.1 Hz, 2H), 3.64 and 3.58 (t, J = 5.1 Hz,2H), 3.30 and 3.13 (s, 3H). 2-153 δ 8.50 and 8.43 (d, J = 2.1 Hz, 1H),7.75-7.85 (m, 1H), 7.3-7.75 (m, 4H), 6.63 and 6.53 (bs, 1H), 5.3-5.45and 5.2-5.3 (m, 1H), 4.5-4.95 (m, 6H). 2-155 δ 8.51 and 8.45 (bs, 1H),7.82 and 7.80 (bs, 1H), 7.35-7.75 (m, 4H), 6.56 (bs, 1H), 4.76 and 4.53(d, J = 5.1 Hz, 2H), 3.4-4.3 (m, 6H), 2.5-2.8 (m, 1H), 1.45-2.1 (m, 2H).2-156 δ 8.52 and 8.49 (d, J = 2.1 Hz, 1H), 7.80 (d, J = 2.1 Hz, 1H),7.45-7.75 (m, 4H), 7.02 and 6.47 (bs, 1H), 4.80 and 4.59 (s, 2H), 4.80and 4.57 (d, J = 5.7 Hz, 2H), 4.20 and 4.15 (q, J = 7.2 Hz, 2H), 1.26and 1.21 (t, J = 7.2 Hz, 3H). 2-158 δ 8.50 (d, J = 2.0 Hz, 1H), 7.79 (d,J = 2.0 Hz, 1H), 7.45-7.75 (m, 4H), 6.78 (bs, 1H), 5.8-6.0 (m, 1H),5.1-5, 35 (m, 3H), 4.57 (d, J = 5.8 Hz, 2H), 1.45 (d, J = 6.8 Hz, 3H).2-159 δ 8.51 and 8.46 (d, J = 2.1 Hz, 1H), 7.75-7.85 (m, 1H), 7.35-7.75(m, 4H), 6.47 and 6.42 (bs, 1H), 5.3-5.55 (m, 2H), 4.80 and 4.56 (d, J =5.7 Hz, 2H), 4.79 and 4.59 (s, 2H). 2-160 δ 8.50 and 8.45 (d, J = 1.8Hz, 1H), 7.81 and 7.79 (d, J = 1.8 Hz, 1H), 7.35-7.75 (m, 4H), 6.49 and6.43 (bs, 1H), 4.85 and 4.66 (d, J = 2.1 Hz, 2H), 4.78 and 4.57 (d, J =5.7 Hz, 2H), 2.50 and 2.45 (t, J = 2.1 Hz, 1H). 2-161 δ 8.50 and 8.45(d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J = 2.1 Hz, 1H), 7.25-7.75 (m,9H), 6.45 (bs, 1H), 5.29 and 5.11 (s, 2H), 4.78 and 4.53 (d, J = 6.0 Hz,2H). 2-162 δ 8.49 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and 7.76 (d, J =2.1 Hz, 1H), 7.15-7.75 (m, 6H), 6.87 (t, J = 8.7 Hz, 2H), 6.46 and 6.42(bs, 1H), 5.21 and 5.04 (s, 2H), 4.75 and 4.53 (d, J = 5.7 Hz, 2H), 3.80and 3.79 (s, 3H). 2-163 δ 8.52 and 8.45 (d, J = 2.1 Hz, 1H), 7.80 and7.78 (d, J = 2.1 Hz, 1H), 7.3-7.75 (m, 8H), 6.57 and 6.51 (bs, 1H), 5.47and 5.29 (s, 2H), 4.83 and 4.54 (d, J = 5.7 Hz, 2H). 2-164 δ 8.52 and8.47 (d, J = 2.1 Hz, 1H), 7.80 and 7.73 (d, J = 2.1 Hz, 1H), 7.3-7.75(m, 6H), 6.91 and 6.49 (bs, 1H), 5.57 and 4.39 (s, 2H), 4.82 and 4.58(d, J = 5.7 Hz, 2H). 2-165 δ 8.45-8.8 (m, 2H), 7.79 (t, J = 2.1 Hz, 1H),7.2-7.75 (m, 5H), 6.98 and 6.48 (bs, 1H), 5.46 and 5.31 (bs, 2H), 4.79and 4.56 (d, J = 6.0 Hz, 2H). 2-166 δ 8.51 and 8.45 (d, J = 2.1 Hz, 1H),7.80 and 7.79 (d, J = 2.1 Hz, 1H), 7.35-7.75 (m, 4H), 7.30 and 7.08 (s,1H), 6.57 and 6.42 (bs, 1H), 5.32 and 5.16 (bs, 2H), 4.80 and 4.55 (d, J= 5.7 Hz, 2H). 2-167 δ 8.51 and 8.46 (d, J = 2.4 Hz, 1H), 7.83 and 7.79(d, J = 2.4 Hz, 1H), 7.3-7.75 (m, 5H), 6.40 (bs, 1H), 5.34 and 5.16 (bs,2H), 4.76 and 4.57 (d, J = 6.0 Hz, 2H). 2-168 δ 8.51 and 8.44 (d, J =2.1 Hz, 1H), 8.42 and 8.31 (d, J = 2.1 Hz, 1H), 7.25-7.85 (m, 7H), 6.37(bs, 1H), 5.27 and 5.09 (s, 2H), 4.78 and 4.53 (d, J = 5.7 Hz, 2H).2-169 δ 8.54 and 8.43 (d, J = 2.1 Hz, 1H), 8.25-8.4 (m, 1H), 7.83 and7.80 (d, J = 2.1 Hz, 1H), 7.05-7.75 (m, 6H), 6.51 (bs, 1H), 5.28 and5.08 (s, 2H), 4.84 and 4.54 (d, J = 5.7 Hz, 2H). 2-171 δ 8.52 and 8.42(d, J = 2.1 Hz, 1H), 7.81 and 7.77 (d, J = 2.1 Hz, 1H). 7.2-7.7 (m, 9H),6.45 and 6.40 (bs, 1H), 5.41 and 5.25 (q, J = 6.6 Hz, 1H), 4.75-7.85 and4.45-4.55 (m, 2H), 1.66 and 1.47 (d, J = 6.6 Hz, 3H). 2-172 δ 8.52 (d, J= 2.0 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.15-7.75 (m, 9H), 6.40 (bs,1H), 5.25 (q, J = 6.6 Hz, 1H), 4.50 (dd, J = 5.1, 1.7 Hz, 2H), 1.47 (d,J = 6.6 Hz, 3H). 2-175 δ 8.54 and 8.39 (d, J = 2.1 Hz, 1H), 7.82 and7.74 (d, J = 2.1 Hz, 1H), 7.2-7.7 (m, 9H), 6.55 and 6.35 (bs, 1H), 4.87and 4.49 (d, J = 6.3 Hz, 2H), 1.74 and 1.62 (s, 6H). 2-176 δ 8.50 and8.47 (d, J = 2.1 Hz, 1H), 7.82 and 7.76 (d, J = 2.1 Hz, 1H), 7.0-7.75(m, 9H), 6.44 and 6.27 (bs, 1H), 4.69 and 4.54 (d, J = 5.7 Hz, 2H), 4.47and 4.28 (t, J = 7.2 Hz, 2H), 3.06 and 2.92 (t, J = 7.2 Hz, 2H). 2-177 δ8.54 and 8.48 (dd, J = 2.1, 0.9 Hz, 1H), 7.0-7.9 (m, 10H), 6.61 (bs,1H), 4.99 and 4.70 (d, J = 5.7 Hz, 2H). 2-178 δ 7.92 and 7.90 (d, J =7.7 Hz, 1H), 7.4-7.75 (m, 4H), 6.39 (bs, 1H), 4.70 and 4.51 (d, J = 6.3and 5.2 Hz, 2H), 4.32 and 4.14 (q, J = 7.0 Hz, 2H), 1.35 and 1.22 (t, J= 7.0 Hz, 3H). 2-179 δ 7.92 and 8.89 (d, J = 8.3 Hz, 1H), 7.4-7.75 (m,4H), 6.39 (bs, 1H), 4.70 and 4.51 (d, J = 6.3 and 5.6 Hz, 2H), 4.52 and4.38 (sep, J = 6.3 Hz, 1H), 1.33 and 1.19 (d, J = 6.3 Hz, 6H). 2-180 δ7.4-7.75 (m, 5H), 6.53 and 6.43 (s, 1H), 4.75-4.8 and 4.5-4.6 (m, 2H),4.3-4.4 and 3.6-3.7 (m, 1H), 4.00 and 3.99 (bs, 3H), 1.33 and 1.21 (d, J= 6.3 Hz, 6H). 2-184 δ 8.79 (bs, 1H), 8.00 (bs, 1H), 7.5-7.7 (m, 4H),6.72 (bs, 1H), 5.25-5.35 (m, 1H), 3.88 (s, 3H), 1.47 (d, J = 6.9 Hz,3H). 2-186 δ 8.79 (bs, 1H), 7.99 (bs, 1H), 7.5-7.7 (m, 4H), 6.74 (bs,1H), 5.2-5.35 (m, 1H), 4.12 (q, J = 7.2 Hz, 2H), 1.47 (d, J = 6.9 Hz,3H), 1.21 (t, J = 7.2 Hz, 3H). 2-188 δ 8.78 (bs, 1H), 7.98 (bs, 1H),7.5-7.7 (m, 4H), 6.78 (bs, 1H), 5.2-5.35 (m, 1H), 4.3-4.45 (m, 1H), 1.46(d, J = 6.9 Hz, 3H), 1.18 (d, J = 6.3 Hz, 6H). 2-195 δ 8.82 (d, J = 1.9Hz, 1H), 8.02 (d, J = 1.9 Hz, 1H), 7.15-7.8 (m, 9H), 6.37 (bs, 1H), 5.26(q, J = 6.4 Hz, 1H), 4.54 (dd, J = 5.5, 1.8 Hz, 2H), 1.48 (d, J = 6.4Hz, 3H). 2-196 δ 8.82 (d, J = 2.0 Hz, 1H), 8.02 (d, J = 2.0 Hz, 1H),6.85-7.75 (m, 8H), 6.35 (bs, 1H), 5.24 (q, J = 6.5 Hz, 1H), 4.53 (d, J =5.5 Hz, 2H), 1.46 (d, J = 6.5 Hz, 3H). 2-197 δ 8.23 and 8.20 (d, J = 2.8Hz, 1H), 7.35-7.75 (m, 4H), 7.29 and 7.27 (d, J = 2.8 Hz, 1H), 6.64 and6.59 (bs, 1H), 4.76 and 4.52 (d, J = 5.8 and 5.0 Hz, 2H), 4.50 and 4.36(sep, J = 6.2 Hz, 1H), 3.89 and 3.88 (s, 3H), 1.33 and 1.19 (d, J = 6.2Hz, 6H). 2-198 δ 8.75 and 8.72 (d, J = 1.8 Hz, 1H), 8.06 and 8.04 (d, J= 1.8 Hz, 1H), 7.35-7.75 (m, 4H), 6.62 (bs, 1H), 4.79 and 4.54 (d, J =6.0 and 4.9 Hz, 2H), 4.55 and 4.37 (sep, J = 6.3 Hz, 1H), 4.04 and 4.03(s, 3H), 2.24 and 2.21 (s, 3H), 1.34 and 1.18 (d, J = 6.3 Hz, 6H). 2-199δ 8.80 and 8.74 (d, J = 1.7 Hz, 1H), 8.05 and 8.03 (d, J = 1.7 Hz, 1H),7.35-7.75 (m, 4H), 6.42 (bs, 1H), 4.77 and 4.56 (d, J = 6.1 and 5.1 Hz,2H), 4.34 and 4.15 (q, J = 7.0 Hz, 2H), 1.37 and 1.22 (t, J = 7.0 Hz,3H). 2-200 δ 8.80 and 8.74 (d, J = 2.1 Hz, 1H), 8.05 and 8.02 (d, J =2.1 Hz, 1H), 7.35-7.8 (m, 4H), 6.44 (bs, 1H), 4.77 and 4.56 (d, J = 6.0Hz, 2H), 4.54 and 4.39 (sep, J = 6.3 Hz, 1H), 1.35 and 1.19 (d, J = 6.3Hz, 6H). 2-201 δ 8.80 and 8.75 (d, J = 2.0 and 1.7 Hz, 1H), 8.05 and8.04 (d, J = 2.0 and 1.7 Hz, 1H), 7.4-7.75 (m, 4H), 6.49 and 6.42 (bs,1H), 4.79 and 4.57 (d, J = 6.1 and 5.5 Hz, 2H), 4.34 and 4.15 (d, J =7.2 Hz, 2H), 1.0-1.3 (m, 1H), 0.45-0.65 (m, 2H), 0.15-0.35 (m, 2H).2-202 δ 8.81 and 8.70 (d, J = 2.0 Hz, 1H), 8.04 and 8.00 (d, J = 2.0 Hz,1H), 7.15-7.55 (m, 9H), 6.40 and 6.32 (bs, 1H), 5.43 and 5.26 (q, J =6.6 Hz, 1H), 4.5-4.85 (m, 2H), 1.68 and 1.47 (d, J = 6.6 Hz, 3H). 2-204δ 8.44 and 8.39 (d, J = 2.4 Hz, 1H), 7.45-7.75 (m, 5H), 6.52 (bs, 1H),4.77 and 4.53 (d, J = 6.1 and 5.1 Hz, 2H), 4.21 and 4.03 (t, J = 6.8 Hz,2H), 1.7-1.85 and 1.55-1.7 (m, 2H), 0.97 and 0.86 (t, J = 7.3 Hz, 3H).2-206 δ 7.2-8.5 (m, 12H), 6.28 (d, J = 7.2 Hz, 1H), 3.92 (s, 3H). 2-207δ 8.49 (d, J = 2.1 Hz, 1H), 7.45-7.8 (m, 5H), 6.78 (bs, 1H), 5.15-5.3(m, 1H), 4.06 (t, J = 6.9 Hz, 2H), 1.5-1.65 (m, 2H), 1.44 (d, J = 6.9Hz, 3H), 1.2-1.4 (m, 2H), 0.87 (t, J = 6.9 Hz, 3H). 2-208 δ 8.49 (d, J =2.1 Hz, 1H), 7.45-7.8 (m, 5H), 6.75 (bs, 1H), 5.15-5.3 (m, 1H), 3.84 (d,J = 6.6 Hz, 2H), 1.8-2.0 (m, 1H), 1.45 (d, J = 6.6 Hz, 3H), 0.83 (d, J =6.6 Hz, 6H). 2-209 δ 8.50 (d, J = 2.1 Hz, 1H), 7.45-7.85 (m, 5H), 6.81(bs, 1H), 5.15-5.35 (m, 1H), 3.88 (d, J = 7.2 Hz, 2H), 1.44 (d, J = 6.9Hz, 3H), 1.0-1.15 (m, 1H), 0.45-0.55 (m, 2H), 0.15-0.25 (m, 2H). 2-210 δ8.49 (d, J = 2.1 Hz, 1H), 7.78 (d, J = 2.1 Hz, 1H). 7.5-7.65 (m, 4H),6.87 (bs, 1H), 5.2-5.3 (m, 1H), 1.44 (d, J = 6.6 Hz, 3H), 1.23 (s, 9H).2-211 δ 8.49 (d, J = 2.1 Hz, 1H), 7.45-7.8 (m, 5H), 6.52 (bs, 1H), 4.51(d, J = 5.1 Hz, 2H), 3.85-4.0 (m, 1H), 1.4-1.65 (m, 4H), 0.83 (t, J =7.5 Hz, 6H). 2-213 δ 8.49 (d, J = 2.1 Hz, 1H), 7.45-7.8 (m, 5H), 6.49(bs, 1H), 5.75-5.9 (m, 1H), 5.05-5.2 (m, 2H), 4.6-4.75 (m, 1H), 4.53 (d,J = 5.1 Hz, 2H), 1.26 (d, J = 6.6 Hz, 3H). 2-214 δ 7.90 (d, J = 7.8 Hz,1H), 7.45-7.75 (m, 4H), 6.3-6.45 (m, 1H), 4.52 (d, J = 4.9 Hz, 2H), 4.14(q, J = 7.1 Hz, 2H), 1.22 (t, J = 7.1 Hz, 3H). 2-219 δ 8.80 (d, J = 2.0Hz, 1H), 8.00 (d, J = 2.0 Hz, 1H), 7.45-7.75 (m, 4H), 6.49 (bs, 1H),4.56 (d, J = 5.5 Hz, 2H), 3.97 (qui, J = 6.1 Hz, 1H), 1.45-1.65 (m, 4H),0.83 (t, J = 7.3 Hz, 6H). 2-220 δ 8.80 (d, J = 2.0 Hz, 1H), 8.00 (d, J =2.0 Hz, 1H), 7.45-7.75 (m, 4H), 6.47 (bs, 1H), 5.85 (ddd, J = 17.3,10.7, 6.2 Hz, 1H), 5.05-5.2 (m, 2H), 4.71 (qd, J = 6.8, 6.2 Hz, 1H),4.58 (d, J = 5.1 Hz, 2H), 1.27 (d, J = 6.8 Hz, 3H). 2-222 δ 8.43 and8.39 (d, J = 2.4 Hz, 1H), 7.3-7.75 (m, 5H), 6.59 and 6.57 (t, J = 72.0Hz, 1H), 6.49 and 6.42 (bs, 1H), 4.75 and 4.54 (d, J = 6.3 Hz, 2H), 4.07and 3.89 (s, 3H). 2-224 δ 8.51 and 8.40 (d, J = 2.1 Hz, 1H), 7.35-7.85(m, 5H), 6.55-6.75 (m, 2H), 5.75-5.95 (m, 1H), 5.35-5.55 (m, 1H),4.3-4.8 (m, 3H), 1.33 and 1.19 (d, J = 6.0 Hz, 6H). 2-226 δ 8.56 (d, J =1.7 Hz, 1H), 7.80 (d, J = 1.7 Hz, 1H), 7.5-7.75 (m, 4H), 6.57 (bs, 1H),4.53 (d, J = 5.1 Hz, 2H), 4.36 (sep, J = 6.3 Hz, 1H), 1.17 (d, J = 6.3Hz, 6H), 0.27 (s, 9H). 2-227 δ 8.45-8.65 (m, 1H), 6.35-7.8 (m, 10H),4.3-4.85 (m, 3H), 1.15-1.4 (m, 6H). 2-228 δ 8.85-8.95 (m, 1H), 6.35-8.2(m, 9H), 4.3-4.85 (m, 3H), 1.15-1.4 (m, 6H). 2-229 δ 8.91 (d, J = 2.1Hz, 1H), 8.65 (bs, 1H), 8.15-8.2 (m, 2H), 7.5-7.75 (m, 4H), 6.55 (bs,1H), 4.58 (d, J = 6.6 Hz, 2H), 4.3-4.45 (m, 1H), 1.20 (d, J = 6.6 Hz,6H). 2-232 δ 8.70 and 8.64 (s, 1H), 7.4-7.8 (m, 4H), 6.40 (bs, 1H),4.3-4.75 (m, 3H), 1.33 and 1.20 (d, J = 6.6 Hz, 6H). 2-234 δ 8.63 (d, J= 2.1 Hz, 1H), 8.11 (d, J = 2.1 Hz, 1H), 7.5-7.75 (m, 4H), 6.5-7.0 (m,1H), 5.15-5.35 (m, 1H), 3.87 (s, 3H), 1.47 (d, J = 6.6 Hz, 3H). 2-237 δ8.63 (bs, 1H), 8.1-8.15 (m, 1H), 7.5-7.75 (m, 4H), 6.5-7.0 (m, 1H),5.15-5.35 (m, 1H), 4.13 (q, J = 7.2 Hz, 2H), 1.46 (d, J = 6.9 Hz, 3H),1.21 (t, J = 7.2 Hz, 3H). 2-238 δ 8.63 and 8.58 (d, J = 2.1 Hz, 1H),8.14 and 8.10 (d, J = 2.1 Hz, 1H), 7.1-7.75 (m, 4H), 6.43 (bs, 1H), 4.75and 4.52 (d, J = 5.7 Hz, 2H), 4.21 and 4.03 (t, J = 6.9 Hz, 2H),1.3-1.85 (m, 2H), 0.97 and 0.86 (t, J = 7.5 Hz, 3H). 2-242 δ 8.51 (d, J= 2.1 Hz, 1H), 7.15-7.8 (m, 9H), 6.41 (bs, 1H), 5.06 (s, 2H), 4.53 (d, J= 5.1 Hz, 2H). 2-243 δ 8.51 (d, J = 2.1 Hz, 1H), 6.9-7.85 (m, 8H), 6.39(bs, 1H), 5.03 (s, 2H), 4.54 (d, J = 5.4 Hz, 2H). 2-244 δ 8.59 (d, J =2.0 Hz, 1H), 7.94 (d, J = 2.0 Hz, 1H), 7.15-7.7 (m, 9H), 6.41 (bs, 1H),5.24 (q, J = 6.5 Hz, 1H), 4.99 (dd, J = 5.1, 1.7 Hz, 2H), 1.47 (d, J =6.5 Hz, 3H). 2-247 δ 8.31 and 8.27 (d, J = 2.7 Hz, 1H), 7.25-7.75 (m,7H), 6.95-7.1 (m, 2H), 6.52 (bs, 1H), 4.76 and 4.54 (d, J = 5.8 and 5.1Hz, 2H), 4.06 and 3.89 (s, 3H). 2-249 δ 8.65 and 8.59 (d, J = 1.7 Hz,1H), 7.91 and 7.87 (d, J = 1.7 Hz, 1H), 7.35-7.75 (m, 9H), 6.59 (bs,1H), 4.80 and 4.56 (d, J = 5.8 and 5.1 Hz, 2H), 4.54 and 4.38 (sep, J =6.3 Hz, 1H), 1.34 and 1.19 (d, J = 6.3 Hz, 6H). 2-251 δ 8.63 and 8.58(d, J = 1.5 Hz, 1H), 8.15 and 8.12 (d, J = 1.5 Hz, 1H), 7.45-7.9 (m,4H), 6.48 (bs, 1H), 4.78 and 4.55 (d, J = 5.4 Hz, 2H), 4.61 and 4.41 (q,J = 8.4 Hz, 2H). 2-254 δ 8.50 (d, J = 2.1 Hz, 1H), 7.79 (d, J = 2.1 Hz,1H), 7.5-7.75 (m, 4H), 6.80 (bs, 1H), 5.15-5.35 (m, 1H), 4, 02 (t, J =6.9 Hz, 2H), 1.5-1.7 (m, 2H), 1.45 (d, J = 6.9 Hz, 3H), 0.86 (t, J = 7.5Hz, 3H). 2-255 δ 8.30 and 8.26 (d, J = 2.4 Hz, 1H), 7.3-7.75 (m, 6H),7.33 and 7.30 (d, J = 2.4 Hz, 1H), 6.95-7.1 (m, 2H), 6.58 (bs, 1H), 4.77and 4.53 (d, J = 5.8 and 4.8 Hz, 2H), 4.51 and 4.37 (sep, J = 6.3 Hz,1H), 1.33 and 1.20 (d, J = 6.3 Hz, 6H). 2-256 δ 8.50 and 8.44 (d, J =1.7 Hz, 1H), 7.75 and 7.72 (d, J = 1.7 Hz, 1H), 7.35-7.75 (m, 4H), 6.55(bs, 1H), 4.77 and 4.52 (d, J = 6.1 and 5.1 Hz, 2H), 4.51 and 4.36 (sep,J = 6.5 Hz, 1H), 2.09 and 2.08 (s, 3H), 1.33 and 1.18 (d, J = 6.5 Hz,6H). 2-257 δ 8.43 (d, J = 1.7 Hz, 1H), 7.35-7.75 (m, 4H), 7.74 (d, J =1.7 Hz, 1H), 6.59 (bs, 1H), 4.77 (d, J = 5.1 Hz, 2H), 4.36 (sep, J = 4.4Hz, 1H), 1.45-1.55 (m, 1H), 1.20 (d, J = 4.4 Hz, 6H), 0.85-0.95 (m, 4H).2-258 δ 8.49 and 8.44 (d, J = 1.7 Hz, 1H), 7.76 and 7.73 (d, J = 1.7 Hz,1H). 7.3-7.7 (m, 4H), 6.62 (bs, 1H), 4.78 and 4.53 (d, J = 5.8 and 4.8Hz, 2H), 4.52 and 4.36 (sep, J = 6.5 Hz, 1H), 2.75-2.95 (m, 1H),1.9-2.15 (m, 2H), 1.5-1.9 (m, 6H), 1.34 and 1.18 (d, J = 6.5 Hz, 6H).2-259 δ 8.57 and 8.51 (d, J = 1.7 Hz, 1H), 7.82 and 7.79 (d, J = 1.7 Hz,1H), 7.3-7.75 (m, 4H), 6.52 (bs, 1H), 4.77 and 4.53 (d, J = 5.8 and 5.1Hz, 2H), 4.52 and 4.38 (sep, J = 6.5 Hz, 1H), 1.33 and 1.18 (d, J = 6.5Hz, 6H). 2-260 δ 8.57 and 8.52 (d, J = 2.0 Hz, 1H), 7.83 and 7.79 (d, J= 2.0 Hz, 1H), 7.25-7.75 (m, 4H), 6.52 (bs, 1H), 4.77 and 4.53 (d, J =5.8 and 4.8 Hz, 2H). 4.50 and 4.36 (sep, J = 6.1 Hz, 1H), 1.33 and 1.18(d, J = 6.1 Hz, 6H). 2-261 δ 8.56 and 8.50 (d, J = 1.7 Hz, 1H), 7.81 and7.77 (d, J = 1.7 Hz, 1H), 7.3-7.75 (m, 4H), 6.52 (bs, 1H), 4.77 and 4.53(d, J = 6.1 and 5.1 Hz, 2H), 4.52 and 4.36 (sep, J = 6.3 Hz, 1H), 1.33and 1.18 (d, J = 6.3 Hz, 6H). 2-262 δ 8.54 and 8.48 (d, J = 1.7 Hz, 1H),7.80 and 7.77 (d, J = 1.7 Hz, 1H), 7.35-7.75 (m, 4H), 6.55 (bs, 1H),4.78 and 4.54 (d, J = 5.1 Hz, 2H), 4.53 and 4.36 (sep, J = 6.5 Hz, 1H),2.07 (bs, 1H), 1.64 and 1.57 (s, 6H), 1.34 and 1.19 (d, J = 6.5 Hz, 6H).2-263 δ 8.53 and 8.47 (d, J = 1.7 Hz, 1H), 7.79 and 7.76 (d, J = 1.7 Hz,1H), 7.3-7.75 (m, 4H), 6.54 (bs, 1H), 4.77 and 4.53 (d, J = 6.1 and 4.8Hz, 2H), 4.51 and 4.36 (sep, J = 6.3 Hz, 1H), 1.7-2.15 (m, 8H), 1.33 and1.18 (d, J = 6.3 Hz, 6H). 2-264 δ 8.55 and 8.49 (d, J = 1.7 Hz, 1H),7.81 and 7.78 (d, J = 1.7 Hz, 1H), 7.45-7.75 (m, 4H), 6.57 (bs, 1H),4.77 and 4.53 (d, J = 6.1 and 5.1 Hz, 2H), 4.50 and 4.36 (sep, J = 6.3Hz, 1H), 1.55-2.05 (m, 10H), 1.33 and 1.18 (d, J = 6.3 Hz, 6H). 2-265 δ8.54 and 8.49 (d, J = 1.7 Hz, 1H), 7.81 and 7.77 (d, J = 1.7 Hz, 1H),7.35-7.75 (m, 4H), 6.59 (bs, 1H), 6.24 (bs, 1H), 4.78 and 4.53 (d, J =6.1 and 4.8 Hz, 2H), 4.52 and 4.36 (sep, J = 6.1 Hz, 1H), 2.45-2.65 (m,4H), 1.9-2.05 (m, 2H), 1.33 and 1.18 (d, J = 6.1 Hz, 6H). 2-266 δ 8.52and 8.46 (d, J = 1.7 Hz, 1H), 7.78 and 7.75 (d, J = 1.7 Hz, 1H),7.3-7.75 (m, 4H), 6.56 (bs, 1H), 6.30 (bs, 1H), 4.78 and 4.53 (d, J =5.8 and 4.8 Hz, 2H), 4.52 and 4.36 (sep, J = 6.5 Hz, 1H), 2.1-2.3 (m,4H), 1.55-1.75 (m, 4H), 1.33 and 1.18 (d, J = 6.5 Hz, 6H). 2-267 δ 8.63and 8.58 (d, J = 1.7 Hz, 1H), 7.90 and 7.86 (d, J = 1.7 Hz, 1H),7.35-7.75 (m, 8H), 6.63 (bs, 1H), 4.80 and 4.56 (d, J = 5.8 and 5.1 Hz,2H), 4.55 and 4.38 (sep, J = 6.5 Hz, 1H), 1.35 and 1.20 (d, J = 6.5 Hz,6H), 1.34 (s, 9H). 2-268 δ 8.72 and 8.66 (d, J = 1.7 Hz, 1H), 8.6-8.65(m, 1H), 7.98 and 7.94 (d, J = 1.7 Hz, 1H), 7.3-7.75 (m, 7H), 6.59 (bs,1H), 4.81 and 4.57 (d, J = 5.1 Hz, 2H), 4.54 and 4.38 (sep, J = 6.1 Hz,1H), 1.36 and 1.21 (d, J = 6.1 Hz, 6H). 2-269 δ 8.78 and 8.77 (d, J =1.0 Hz, 1H), 8.67 and 8.62 (d, J = 1.7 Hz, 1H), 8.55-8.6 (m, 1H), 7.93and 7.90 (d, J = 1.7 Hz, 1H), 7.85 and 7.82 (t, J = 2.0 Hz, 1H), 7.3-7.8(m, 5H), 6.70 (bs, 1H), 4.81 and 4.57 (d, J = 5.1 Hz, 2H), 4.53 and 4.35(sep, J = 6.5 Hz, 1H), 1.36 and 1.21 (d, J = 6.5 Hz, 6H). 2-270 δ8.55-8.7 (m, 3H), 7.94 and 7.91 (d, J = 2.0 Hz, 1H), 7.45-7.75 (m, 4H),7.40 (d, J = 6.3 Hz, 2H), 6.72 (bs, 1H), 4.81 and 4.57 (d, J = 5.8 Hz,2H), 4.52 and 4.39 (sep, J = 6.1 Hz, 1H), 1.36 and 1.21 (d, J = 6.1 Hz,6H). 2-271 δ 8.72 and 8.71 (d, J = 2.0 Hz, 1H), 7.89 and 7.83 (d, J =2.0 Hz, 1H), 7.05-7.75 (m, 8H), 6.81 and 6.64 (bs, 1H), 4.75 and 4.58(d, J = 6.1 and 5.1 Hz, 2H), 4.39 and 4.06 (sep, J = 6.3 Hz, 1H), 1.21and 0.98 (d, J = 6.3 Hz, 6H). 3-002 δ 6.75-7.75 (m, 12H), 5.45-5.6 and5.1-5.2 (m, 1H), 5.17 and 5.04 (ds, 2H), 1.54 and 1.37 (d, J = 7.2 Hz,3H). 3-003 δ 7.1-7.5 (m, 7H), 6.51 (bs, 1H), 5.25-5.4 and 5.0-5.15 (m,1H), 4.00 and 3.85 (s, 3H), 2.44 and 2.35 (s, 3H), 1.60 and 1.45 (d, J =6.9 Hz, 3H). 3-004 δ 8.51 and 8.49 (d, J = 2.0 Hz, 1H), 7.95-8.15 (m,1H), 7.78 and 7.77 (d, J = 2.0 Hz, 1H), 7.0-7.65 (m, 3H), 7.53 (bs, 1H),4.79 and 4.57 (dd, J = 6.1, 1.5 Hz and 4.8, 1.5 Hz, 2H), 4.34 and 4.17(q, J = 7.0 Hz, 2H), 1.38 and 1.25 (t, J = 7.0 Hz, 3H). 3-005 δ 8.51 and8.47 (d, J = 2.0 Hz, 1H), 7.80 and 7.78 (d, J = 2.0 Hz, 1H), 7.25-7.45(m, 1H), 6.85-7.0 (m, 2H), 6.66 and 6.61 (bs, 1H), 4.76 and 4.56 (d, J =6.1 and 5.1 Hz, 2H), 4.32 and 4.15 (q, J = 7.2 Hz, 2H), 1.36 and 1.22(t, J = 7.2 Hz, 3H). 3-006 δ 8.51 and 8.47 (d, J = 2.0 Hz, 1H), 7.79 and7.78 (d, J = 2.0 Hz, 1H), 7.25-7.7 (m, 4H), 6.97 and 6.89 (bs, 1H), 4.77and 4.56 (d, J = 6.1 and 5.1 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz, 2H),1.37 and 1.23 (t, J = 7.0 Hz, 3H). 3-007 δ 8.50 (d, J = 2.1 Hz, 1H),7.77 (d, J = 2.1 Hz, 1H), 7.6-7.7 (m, 1H), 7.25-7.45 (m, 3H), 6.96 (bs,1H), 4.55 (d, J = 5.1 Hz, 2H), 4.05 (t, J = 6.9 Hz, 2H), 1.55-1.7 (m,2H), 0.87 (t, J = 7.5 Hz, 3H). 3-008 δ 8.51 and 8.46 (d, J = 2.0 Hz,1H), 7.80 and 7.78 (d, J = 2.0 Hz, 1H), 7.1-7.35 (m, 2H), 6.9-7.1 (m,1H), 6.48 and 6.40 (bs, 1H), 4.79 and 4.58 (d, J = 6.1 and 5.1 Hz, 2H),4.31 and 4.14 (q, J = 7.0 Hz, 2H), 1.36 and 1.22 (t, J = 7.0 Hz, 3H).3-009 δ 8.51 and 8.46 (d, J = 2.0 Hz, 1H), 7.80 and 7.78 (d, J = 2.0 Hz,1H), 7.15-7.35 (m, 3H), 6.40 and 6.34 (bs, 1H), 4.81 and 4.60 (d, J =6.1 and 5.1 Hz, 2H), 4.31 and 4.14 (q, J = 7.0 Hz, 2H), 1.36 and 1.22(t, J = 6.3 Hz, 3H). 3-010 δ 8.51 and 8.47 (d, J = 2.0 Hz, 1H), 7.80 and7.78 (d, J = 2.0 Hz, 1H), 7.2-7.65 (m, 4H), 6.71 and 6.66 (bs, 1H), 4.77and 4.55 (d, J = 6.1 and 5.1 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz, 2H),1.37 and 1.23 (t, J = 7.0 Hz, 3H). 3-011 δ 8.51 (d, J = 2.1 Hz, 1H),7.78 (d, J = 2.1 Hz, 1H), 7.2-7.65 (m, 4H), 6.71 (bs, 1H), 4.55 (d, J =5.1 Hz, 2H), 4.04 (t, J = 6.9 Hz, 2H), 1.55-1.7 (m, 2H), 0.86 (t, J =7.5 Hz, 3H). 3-013 δ 7.8-7.9 (m, 1H), 7.05-7.5 (m, 6H), 6.59 (bs, 1H),5.25-5.4 and 5.0-5.1 (m, 1H), 4.26 and 4.11 (q, J = 7.2 Hz, 2H),1.45-1.65 (m, 3H), 1.34 and 1.20 (t, J = 7.2 Hz, 3H). 3-014 δ 8.52 and8.47 (d, J = 2.0 Hz, 1H), 7.8-7.9 (m, 1H), 7.80 and 7.78 (d, J = 2.0 Hz,1H), 7.2-7.45 (m, 2H), 7.0-7.15 (m, 1H), 6.48 (bs, 1H), 4.77 and 4.54(d, J = 6.1 and 5.1 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz, 2H), 1.37 and1.22 (t, J = 7.0 Hz, 3H). 3-015 δ 8.51 (d, J = 2.1 Hz, 1H), 7.87 (d, J =7.8 Hz, 1H), 7.78 (d, J = 2.1 Hz, 1H), 7.05-7.45 (m, 3H), 6.47 (bs, 1H),4.54 (d, J = 5.4 Hz, 2H), 4.04 (t, J = 6.6 Hz, 2H), 1.5-1.7 (m, 2H),0.86 (t, J = 7.5 Hz, 3H). 3-016 δ 8.51 and 8.47 (d, J = 2.0 Hz, 1H),7.7-8.1 (m, 1H), 7.80 and 7.78 (d, J = 2.0 Hz, 1H), 7.05-7.45 (m, 3H),6.52 and 6.48 (bs, 1H), 4.77 and 4.54 (d, J = 6.1 and 5.1 Hz, 2H), 4.53and 4.48 (sep, J = 6.3 Hz, 1H), 1.34 and 1.19 (d, J = 6.3 Hz, 6H). 3-017δ 8.52 and 8.48 (d, J = 2.0 Hz, 1H), 7.8-7.9 (m, 1H), 7.80 and 7.79 (d,J = 2.0 Hz, 1H), 7.2-7.45 (m, 2H), 7.0-7.15 (m, 1H), 6.48 (bs, 1H), 4.79and 4.55 (d, J = 6.1 and 5.1 Hz, 2H), 4.08 and 3.91 (d, J = 7.2 Hz, 2H),1.0-1.3 (m, 1H), 0.4-0.65 (m, 2H), 0.15-0.35 (m, 2H). 3-018 δ 8.52 and8.43 (d, J = 2.0 Hz, 1H), 7.7-7.9 (m, 1H), 7.80 and 7.75 (d, J = 2.0 Hz,1H), 7.0-7.45 (m, 8H), 6.45 (bs, 1H), 5.42 and 5.27 (q, J = 6.6 Hz, 1H),4.45-4.85 (m, 2H), 1.68 and 1.47 (d, J = 6.6 Hz, 3H). 3-019 δ 8.50 (d, J= 2.1 Hz, 1H), 7.78 (d, J = 2.1 Hz, 1H), 7.15-7.45 (m, 4H), 6.41 (bs,1H), 4.52 (d, J = 5.4 Hz, 2H), 4.03 (t, J = 6.9 Hz, 2H), 2.41 (s, 3H),1.55-1.7 (m, 2H), 0.86 (t, J = 7.8Hz, 3H). 3-020 δ 8.51 and 8.47 (d, J =2.0 Hz, 1H), 7.81 and 7.77 (d, J = 2.0 Hz, 1H), 7.1-7.5 (m, 4H), 6.52(bs, 1H), 4.73 and 4.53 (d, J = 6.0 and 5.5 Hz, 2H), 4.52 and 4.38 (sep,J = 6.3 Hz, 1H), 2.41 and 2.32 (s, 3H), 1.34 and 1.19 (d, J = 6.3 Hz,6H). 3-021 δ 8.51 and 8.48 (d, J = 2.0 Hz, 1H), 7.81 and 7.79 (d, J =2.0 Hz, 1H), 6.95-7.3 (m, 3H), 6.42 (bs, 1H), 4.72 and 4.52 (d, J = 6.1and 5.1 Hz, 2H), 4.31 and 4.14 (q, J = 7.0 Hz, 2H), 2.30 and 2.21 (d, J= 2.4 Hz, 3H), 1.36 and 1.22 (t, J = 7.0 Hz, 3H). 3-023 δ 8.50 and 8.47(d, J = 2.0 Hz, 1H), 7.81 and 7.79 (d, J = 2.0 Hz, 1H), 7.3-8.1 (m, 4H),7.23 and 7.12 (t, J = 55.6 Hz, 1H), 6.64 (bs, 1H), 4.74 and 4.52 (d, J =6.2 and 4.8 Hz, 2H), 4.3-4.65 (m, 1H), 1.34 and 1.20 (d, J = 6.3 Hz,6H). 3-024 δ 8.50 and 8.45 (d, J = 2.0 Hz, 1H), 7.81 and 7.78 (d, J =2.0 Hz, 1H), 7.25-7.65 (m, 3H), 6.53 (bs, 1H), 4.74 and 4.51 (d, J = 6.1and 4.9 Hz, 2H), 4.51 and 4.37 (sep, J = 6.1 Hz, 1H), 1.33 and 1.19 (d,J = 6.1 Hz, 6H). 3-025 δ 8.50 and 8.45 (d, J = 2.0 Hz, 1H), 7.81 and7.79 (d, J = 2.0 Hz, 1H), 7.4-7.6 (m, 2H), 7.25-7.4 (m, 1H), 6.52 and6.45 (bs, 1H), 4.79 and 4.57 (d, J = 6.1 and 5.1 Hz, 2H), 4.31 and 4.14(q, J = 7.0 Hz, 2H), 1.35 and 1.21 (t, J = 7.0 Hz, 3H). 3-026 δ 8.60 and8.31 (bs, 1H), 8.50 and 8.48 (d, J = 2.0 Hz, 1H), 8.17 and 8.12 (dd, J =8.0, 1.8 Hz, 1H), 7.76 (d, J = 2.0 Hz, 1H), 7.35-7.5 (m, 1H), 6.85-7.1(m, 2H), 4.79 and 4.57 (d, J = 5.8 and 4.8 Hz, 2H), 4.33 and 4.18 (q, J= 7.0 Hz, 2H), 3.99 and 3.89 (s, 3H), 1.38 and 1.26 (t, J = 7.0 Hz, 3H).3-027 δ 8.51 and 8.48 (d, J = 2.0 Hz, 1H), 8.09 and 8.02 (dd, J = 7.8,1.9 Hz, 1H), 7.78 and 7.77 (d, J = 2.0 Hz, 1H), 7.62 (bs, 1H), 7.05-7.7(m, 3H), 6.63 and 6.53 (d, J = 73.1 Hz, 1H), 4.77 and 4.55 (d, J = 6.1and 4.8 Hz, 2H), 4.33 and 4.17 (q, J = 7.0 Hz, 2H), 1.37 and 1.24 (t, J= 7.0 Hz, 3H). 3-028 δ 8.51 and 8.47 (d, J = 2.0 and 2.4 Hz, 1H), 8.02and 7.94 (dd, J = 7.9, 2.1 Hz, 1H), 7.79 and 7.78 (d, J = 2.0 and 2.4Hz, 1H), 7.2-7.6 (m, 3H), 7.44 (bs, 1H), 4.77 and 4.54 (d, J = 6.1 and4.8 Hz, 2H), 4.33 and 4.16 (q, J = 7.0 Hz, 2H), 1.37 and 1.22 (t, J =7.0 Hz, 3H). 3-029 δ 8.50 and 8.47 (d, J = 2.0 Hz, 1H), 7.79 and 7.77(d, J = 2.0 Hz, 1H), 7.1-7.6 (m, 4H), 7.01 (bs, 1H), 4.77 and 4.56 (d, J= 6.1 and 5.1 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz, 2H), 2.44 and 2.39(s, 3H), 1.37 and 1.23 (t, J = 7.0 Hz, 3H). 3-030 δ 8.51 and 8.45 (d, J= 2.0 Hz, 1H), 8.05 and 8.00 (dd, J = 7.8, 1.2 Hz, 1H), 7.83 and 7.80(d, J = 2.0 Hz, 1H), 7.35-7.75 (m, 3H), 6.50 (bs, 1H), 4.78 and 4.56 (d,J = 5.8 and 5.5 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz, 2H), 1.36 and1.22 (t, J = 7.0 Hz, 3H). 3-031 δ 8.51 and 8.48 (d, J = 2.0 Hz, 1H),7.81 and 7.79 (d, J = 2.0 Hz, 1H), 7.35-7.85 (m, 4H), 7.07 and 6.99 (bs,1H), 4.80 and 4.57 (d, J = 5.8 and 5.1 Hz, 2H), 4.34 and 4.17 (q, J =7.0 Hz, 2H), 1.37 and 1.23 (t, J = 7.0 Hz, 3H). 3-032 δ 8.42 and 8.31(d, J = 2.0 Hz, 1H), 7.72 and 7.71 (d, J = 2.0 Hz, 1H), 7.25-7.7 (m,9H), 6.05 and 6.03 (bs, 1H), 4.50 and 4.25 (d, J = 6.1 and 5.1 Hz, 2H),4.18 and 4.01 (q, J = 7.0 Hz, 2H), 1.27 and 1.14 (t, J = 7.0 Hz, 3H).3-033 δ 8.45-8.55 (m, 1H), 7.2-7.8 (m, 5H), 6.95 (bs, 1H), 4.75 and 4.55(d, J = 5.7 Hz, 2H), 4.07 and 3.89 (s, 3H). 3-035 δ 8.50 (d, J = 2.1 Hz,1H), 7.7-7.8 (m, 2H), 7.3-7.45 (m, 3H), 7.17 (bs, 1H), 4.56 (d, J = 4.8Hz, 2H), 1.26 (s, 9H). 3-037 δ 8.45-8.55 (m, 1H), 7.2-7.85 (m, 5H), 6.73(bs, 1H), 4.5-4.6 (m, 2H), 3.88 (s, 3H). 3-038 δ 8.51 (d, J = 2.1 Hz,1H), 7.77 (d, J = 2.1 Hz, 1H), 7.5-7.65 (m, 2H), 7.2-7.4 (m, 2H), 6.75(bs, 1H), 4.55 (d, J = 5.1 Hz, 2H), 4.05-4.25 (m, 1H), 1.15-1.7 (m, 5H),0.84 (t, J = 7.8 Hz, 3H). 3-039 δ 8.50 (d, J = 2.1 Hz, 1H), 7.77 (d, J =2.1 Hz, 1H), 7.55-7.65 (m, 2H), 7.2-7.4 (m, 2H), 6.83 (bs, 1H), 4.55 (d,J = 5.4 Hz, 2H), 1.26 (s, 9H). 3-040 δ 8.52 (d, J = 2.1 Hz, 1H), 7.81(d, J = 2.1 Hz, 1H), 7.25-7.7 (m, 4H), 6.68 (bs, 1H), 4.58 (d, J = 5.4Hz, 2H), 4.44 (q, J = 8.4 Hz, 2H). 3-042 δ 8.4-8.55 (m, 1H), 7.0-7.9 (m,5H), 6.54 (bs, 1H), 4.7-4.8 and 4.5-4.6 (m, 2H) , 3.85-4.1 (m, 3H).3-043 δ 8.51 (d, J = 2.1 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H), 7.77 (d, J =2.1 Hz, 1H), 7.3-7.45 (m, 2H), 7.05-7.15 (m, 1H), 6.49 (bs, 1H), 4.54(d, J = 5.1 Hz, 2H), 4.05-4.25 (m, 1H), 1.15-1.7 (m, 5H), 0.84 (t, J =7.5 Hz, 3H). 3-044 δ 8.51 and 8.46 (d, J = 2.1 Hz, 1H), 7.75-7.9 (m,2H), 7.0-7.45 (m, 3H), 6.52 (bs, 1H), 4.78 and 4.54 (d, J = 5.4 Hz, 2H),1.39 and 1.26 (s, 9H). 3-045 δ 8.53 and 8.49 (d, J = 2.1 Hz, 1H),7.8-7.95 (m, 2H), 7.0-7.45 (m, 3H), 6.37 (bs, 1H), 4.35-4.85 (m, 4H).3-046 δ 8.50 and 8.47 (d, J = 2.1 Hz, 1H), 7.79 and 7.78 (d, J = 2.1 Hz,1H), 7.1-7.5 (m, 4H), 6.48 and 6.40 (bs, 1H), 4.71 and 4.53 (d, J = 6.0Hz, 2H), 4.06 and 3.88 (s, 3H), 2.40 and 2.30 (s, 3H). 3-048 δ 8.50 (d,J = 2.1 Hz, 1H), 7.77 (d, J = 2.1 Hz, 1H), 7.15-7.45 (m, 4H), 6.45 (bs,1H), 4.53 (d, J = 5.1 Hz, 2H), 2.43 (s, 3H), 1.26 (s, 9H). 3-051 δ 8.64and 8.60 (d, J = 1.5 Hz, 1H), 8.14 and 8.11 (d, J = 1.5 Hz, 1H), 7.1-7.4(m, 4H), 6.35 and 6.27 (bs, 1H), 4.76 and 4.56 (d, J = 5.4 Hz, 2H), 4.61and 4.41 (q, J = 8.4 Hz, 2H), 2.40 (s, 3H). 4-001 δ 8.43 and 8.36 (d, J= 2.1 Hz, 1H), 7.82 (d, J = 2.1 Hz, 1H), 7.75 (d, J = 7.8 Hz, 1H),7.2-7.35 (m, 1H), 6.95-7.1 (m, 1H), 6.59 (d, J = 7.8 Hz, 1H), 5.83 and4.14 (s, 1H), 3.79 and 3.62 (s, 3H), 1.84 and 1.55 (s, 6H). 4-002 δ 8.47(d, J = 2.4 Hz, 1H), 7.79 (d, J = 2.4 Hz, 1H), 7.45-7.75 (m, 4H), 7.21(bs, 1H), 4.0-4.2 (m, 2H), 1.82 (s, 3H), 1.75 (s, 3H), 1.17 (t, J = 7.2Hz, 3H). 4-004 δ 8.45-8.55 (m, 1H), 7.35-7.75 (m, 5H), 6.59 and 6.43(bs, 1H), 4.05-4.3 (m, 2H), 2.5-3.0 (m, 4H), 1.75-2.15 (m, 2H), 1.2-1.35(m, 3H). 4-006 δ 8.50 and 8.40 (d, J = 2.0 Hz, 1H), 7.80 (d, J = 2.0 Hz,1H), 7.35-7.7 (m, 3H), 6.9-7.15 (m, 1H), 4.88 and 4.62, 4.25 (d, J =3.1, 15.3, 15.3 Hz, 2H), 4.07 and 3.96 (s, 3H), 2.95-3.30 (m, 2H), 1.22and 1.09 (t, J = 7.2 Hz, 3H). 4-008 δ 8.47 and 8.38 (d, J = 2.4 and 2.0Hz, 1H), 7.80 and 7.78 (d, J = 2.4 and 2.0 Hz, 1H), 7.4-7.75 (m, 3H),7.15-7.25 (m, 1H), 4.25-5.3 (m, 4H), 4.08 and 3.91 (s, 3H), 3.38 and3.15 (s, 3H). 4-009 δ 8.50 and 8.40 (d, J = 2.4 Hz, 1H), 7.80 (d, J =2.4 Hz, 1H), 7.35-7.7 (m, 3H), 6.95-7.2 (m, 1H), 5.5-6.0 (m, 1H),5.0-5.35 (m, 2H), 4.89 and 4.57 (d, J = 15.0 Hz, 1H), 4.76 and 4.28 (d,J = 15.0 Hz, 1H), 4.06 and 3.93 (s, 3H), 3.4-3.9 (m, 2H). 4-010 δ 8.47and 8.38 (d, J = 2.4 Hz, 1H), 7.81 and 7.79 (d, J = 2.4 Hz, 1H),7.4-7.75 (m, 3H), 7.1-7.25 (m, 1H), 5.09 and 4.73 (d, J = 9.6 Hz, 1H),4.80 and 4.42 (d, J = 9.6 Hz, 1H), 3.7-4.3 (m, 2H), 4.08 and 3.95 (s,3H), 2.28 and 2.22 (t, J = 2.6 Hz, 1H). 4-011 δ 8.81 and 8.79 (s, 1H),8.00 and 7.98 (s, 1H), 7.35-7.7 (m, 4H), 4.6-5.4 (m, 2H), 4.09 and 3.92(s, 3H), 2.75-2.85 and 2.6-2.7 (m, 1H), 0.35-0.9 (m, 4H). 4-012 δ 8.52and 8.40 (d, J = 2.0 Hz, 1H), 7.3-7.85 (m, 4H), 7.09 and 7.02 (d, J =6.8 Hz, 1H), 3.95-5.1 (m, 4H), 4.27 and 3.94 (s, 3H). 4-013 δ 8.47 and8.44 (d, J = 2.0 Hz, 1H), 7.81 and 7.75 (d, J = 2.0 Hz, 1H), 7.45-7.75(m, 4H), 4.82 and 4.73 (s, 2H), 3.94 and 3.87 (s, 3H), 2.42 and 2.28 (s,3H). 4-014 δ 8.53 and 8.44 (d, J = 2.0 Hz, 1H), 7.82 and 7.79 (d, J =2.0 Hz, 1H), 7.35-7.75 (m, 4H), 4.98 (bs, 2H), 4.06 and 3.90 (s, 3H),3.63 and 3.59 (s, 3H). 4-015 δ 8.52 (bs, 1H), 7.4-7.9 (m, 5H), 5.67 (bs,1H), 4.82 (bs, 1H), 3.94 (s, 3H). 6-001 δ 8.25-8.5 (m, 3H), 7.7-7.85 (m,2H), 7.3-7.4 (m, 1H), 4.76 and 4.54 (d, J = 6.0 Hz, 2H), 4.34 and 4.16(q, J = 7.2 Hz, 2H), 1.38 and 1.23 (t, J = 7.2 Hz, 3H). 6-003 δ8.25-8.55 (m, 3H), 7.7-7.85 (m, 2H), 7.2-7.3 (m, 1H), 4.76 and 4.54 (d,J = 5.7 Hz, 2H), 4.33 and 4.16 (q, J = 7.2 Hz, 2H), 1.38 and 1.23 (t, J= 7.2H, 3H). 6-004 δ 8.3-8.7 (m, 3H), 7.7-7.8 (m, 1H), 7.5-7.6 (m, 1H),7.2-7.35 (m, 1H), 4.74 and 4.52 (d, J = 5.7 Hz, 2H), 4.33 and 4.16 (q, J= 7.2 Hz, 2H), 2.67 and 2.66 (s, 3H), 1.38 and 1.23 (t, J = 7.2 Hz, 3H).6-005 δ 8.75 (dd, J = 4.8, 1.0 Hz, 1H), 8.49 (d, J = 2.0 Hz, 1H), 8.23(bs, 1H), 8.15 (dd, J = 8.2, 1.0 Hz, 1H), 7.75 (d, J = 2.0 Hz, 1H), 7.56(dd, J = 8.2, 4.8 Hz, 1H), 4.55 (d, J = 5.5 Hz, 2H), 4.16 (q, J = 7.0Hz, 2H), 1.23 (t, J = 7.0 Hz, 3H). 6-006 δ 8.45-8.5 (m, 2H), 8.32 (bs,1H), 7.79 (dd, J = 8.1, 1.5 Hz, 1H), 7.73 (d, J = 1.8 Hz, 1H), 7.35 (dd,J = 8.1, 4.5 Hz, 1H), 4.52 (d, J = 5.7 Hz, 2H), 4.35-4.45 (m, 1H), 1.20(d, J = 6.0 Hz, 6H). 6-007 δ 8.51 (dd, J = 4.5, 1.5 Hz, 1H), 8.48 (d, J= 2.1 Hz, 1H), 8.32 (bs, 1H), 8.00 (dd, J = 8.1, 1.5 Hz, 1H), 7.73 (d, J= 2.1 Hz, 1H), 7.26 (dd, J = 8.1, 4.5 Hz, 1H), 4.52 (d, J = 5.7 Hz, 2H),4.35-4.45 (m, 1H), 1.20 (d, J = 6.0 Hz, 6H). 6-008 δ 8.75 (dd, J = 4.8,1.5 Hz, 1H), 8.48 (d, J = 2.1 Hz, 1H), 8.25 (bs, 1H), 8.15 (d, J = 7.8Hz, 1H), 7.74 (d, J = 2.1 Hz, 1H), 7.56 (dd, J = 7.8, 4.8 Hz, 1H), 4.55(d, J = 5.4 Hz, 2H), 4.35-4.45 (m, 1H), 1.20 (d, J = 6.3 Hz, 6H). 7-001δ 8.4-8.5 and 8.3-8.4 (m, 1H), 8.0-8.1 and 7.8-7.85 (m, 1H), 7.15-7.5(m, 5H), 4.65 and 4.60 (d, J = 6.3 Hz, 2H), 4.04 and 3.87 (s, 3H). 7-002δ 8.50 and 8.47 (d, J = 2.1 Hz, 1H), 8.4-8.5 (m, 1H), 8.05-8.2 (m, 1H),7.80 and 7.78 (d, J = 2.1 Hz, 1H), 7.25-7.4 (m, 1H), 6.44 and 6.27 (bs,1H), 4.78 and 4.56 (d, J = 6.0 Hz, 2H), 4.33 and 4.16 (q, J = 7.2 Hz,2H), 1.38 and 1.24 (t, J = 7.2 Hz, 3H). 7-003 δ 8.51 and 8.48 (d, J =2.1 Hz, 1H), 8.08 and 8.00 (d, J = 7.8 Hz, 1H), 7.81 and 7.79 (d, J =2.1 Hz, 1H), 7.72 and 7.69 (d, J = 7.8 Hz, 1H), 7.07 and 7.01 (bs, 1H),4.78 and 4.56 (d, J = 6.3 Hz, 2H). 4.34 and 4.16 (q, J = 7.2 Hz, 2H),1.38 and 1.23 (t, J = 7.2 Hz, 3H). 7-004 δ 8.7-8.8 (m, 1H), 7.89 and7.73 (d, J = 7.8 Hz, 1H), 7.1-7.6 (m, 4H), 6.95 and 6.81 (bs, 1H),5.2-5.35 and 4.95-5.1 (m, 1H), 4.36 and 4.09 (q, J = 7.2 Hz, 2H), 1.60and 1.45 (d, J = 7.2 Hz, 3H), 1.31 and 1.18 (t, J = 7.2 Hz, 3H). 7-006 δ8.4-8.55 (m, 2H), 8.05-8.15 (m, 1H), 7.78 (d, J = 1.8 Hz, 1H), 7.25-7.4(m, 2H), 4.55 (d, J = 5.1 Hz, 2H), 3.89 (s, 3H). 7-007 δ 8.51 (d, J =2.1 Hz, 1H), 8.45-8.5 (m, 1H), 8.1-8.2 (m, 1H), 7.78 (d, J = 2.1 Hz,1H), 7.3-7.4 (m, 2H), 4.56 (d, J = 4.8 Hz, 2H), 4.06 (t, J = 6.9 Hz,2H), 1.55-1.75 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H). 7-008 δ 8.4-8.55 (m,2H), 8.15-8.25 (m, 1H), 7.78 (d, J = 2.4 Hz, 1H), 7.58 (bs, 1H), 7.3-7.4(m, 1H), 4.56 (d, J = 4.8 Hz, 2H), 1.27 (s, 9H). 7-009 δ 8.5-8.55 (m,1H), 8.45-8.5 (m, 1H), 8.05-8.15 (m, 1H), 7.8-7.85 (m, 1H), 7.25-7.4 (m,2H), 4.60 (d, J = 5.4 Hz, 2H), 4.45 (q, J = 8.7 Hz, 2H). 8-001 δ 8.98(s, 1H), 8.89 (d, J = 4.8 Hz, 1H), 8.51 (d, J = 2.0 Hz, 1H), 7.80 (d, J= 2.0 Hz, 1H), 7.48 (d, J = 4.8 Hz, 1H), 6.62 (bs, 1H), 4.53 (d, J = 5.1Hz, 2H), 4.14 (q, J = 7.0 Hz, 2H), 1.22 (t, J = 7.0 Hz, 3H). 9-001 δ8.81 (d, J = 2.1 Hz, 1H), 8.76 (d, J = 2.1 Hz, 1H), 8.48 (d, J = 2.1 Hz,1H), 8.03 (bs, 1H), 7.77 (d, J = 2.1 Hz, 1H), 4.56 (d, J = 5.8 Hz, 2H),3.90 (s, 3H). 9-002 δ 8.81 (d, J = 2.4 Hz, 1H), 8.77 (d, J = 2.4 Hz,1H), 8.10 (bs, 1H), 7.44 (d, J = 2.1 Hz, 1H), 7.30 (dd, J = 8.1, 2.1 Hz,1H), 7.16 (d, J = 8.1 Hz, 1H), 5.0-5.15 (m, 1H), 4.12 (q, J = 7.2 Hz,2H), 1.48 (d, J = 6.9 Hz, 3H), 1.21 (t, J = 7.2 Hz, 3H). 9-004 δ 8.82and 8.79 (d, J = 2.4 Hz, 1H), 8.77 and 8.71 (d, J = 2.4 Hz, 1H), 8.50and 8.48 (d, J = 2.0 Hz, 1H), 8.08 (bs, 1H), 7.78 and 7.77 (d, J = 2.0Hz, 1H), 4.82 and 4.57 (d, J = 6.1 and 5.5 Hz, 2H), 4.01 and 3.92 (d, J= 7.0 Hz, 2H), 1.0-1.2 (m, 1H), 0.45-0.65 (m, 2H), 0.15-0.4 (m, 2H).9-007 δ 8.82 (d, J = 2.7 Hz, 1H), 8.76 (d, J = 2.7 Hz, 1H), 8.49 (d, J =1.8 Hz, 1H), 8.05 (bs, 1H), 7.76 (d, J = 1.8 Hz, 1H), 4.56 (d, J = 5.1Hz, 2H), 4.35-4.45 (m, 1H), 1.20 (d, J = 6.3 Hz, 6H). 10-001 δ 8.50 and8.48 (d, J = 2.1 Hz, 1H), 7.78 and 7.76 (d, J = 2.1 Hz, 1H), 7.44 and7.40 (d, J = 2.1 Hz, 1H), 7.16 (bs, 1H), 6.57 and 6.54 (d, J = 2.1 Hz,1H), 4.74 and 4.51 (d, J = 5.4 Hz, 2H), 4.25-4.4 and 4.05-4.25 (m, 2H),1.38 and 1.24 (t, J = 7.2 Hz, 3H). 10-002 δ 8.50 (d, J = 2.0 Hz, 1H),7.76 (d, J = 2.0 Hz, 1H), 7.31 (d, J = 1.4 Hz, 1H), 6.91 (s, 1H), 6.32(d, J = 1.4 Hz, 1H), 4.48 (d, J = 5.1 Hz, 2H), 4.16 (q, J = 7.0 Hz, 2H),2.36 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H). 11-001 δ 8.49 and 8.46 (d, J =2.0 Hz, 1H), 7.77 and 7.75 (d, J = 2.0 Hz, 1H), 6.33 (bs, 1H), 6.00 and5.86 (s, 1H), 4.66 and 4.44 (d, J = 6.1 and 5.1 Hz, 2H), 4.31 and 4.14(q, J = 7.0 Hz, 2H), 2.50 and 2.45 (s, 3H), 2.24 and 2.22 (s, 3H), 1.36and 1.23 (t, J = 7.0 Hz, 3H). 11-002 δ 8.50 and 8.46 (d, J = 2.0 Hz,1H), 7.79 and 7.77 (d, J = 2.0 Hz, 1H), 6.69 (bs, 1H), 6.34 and 6.27 (s,1H), 4.69 and 4.47 (d, J = 5.5 and 4.8 Hz, 2H), 4.31 and 4.15 (q, J =7.0 Hz, 2H), 2.36 and 2.33 (s, 3H), 1.36 and 1.23 (t, J = 7.0 Hz, 3H).11-003 δ 8.51 and 8.48 (d, J = 2.4 and 2.0 Hz, 1H), 7.81 and 7.79 (d, J= 2.4 and 2.0 Hz, 1H), 7.65-7.75 (m, 2H), 7.3-7.5 (m, 3H), 6.95 and 6.88(s, 1H), 6.82 and 6.80 (bs, 1H), 4.74 and 4.51 (d, J = 5.8 and 4.8 Hz,2H), 4.33 and 4.16 (q, J = 7.0 Hz, 2H), 1.37 and 1.24 (t, J = 7.0 Hz,3H). 12-001 δ 6.85-7.8 (m, 7H), 5.4-5.55 and 5.05-5.15 (m, 1H), 4.03 and3.88 (s, 3H), 2.55 and 2.51 (s, 3H), 1.54 and 1.35 (d, J = 6.9 Hz, 3H).12-002 δ 6.85-7.75 (m, 11H), 5.4-5.55 and 5.05-5.15 (m, 1H), 5.20 and5.07 (s, 2H), 2.47 and 2.37 (s, 3H), 1.54 and 1.34 (d, J = 6.9 Hz, 3H).12-003 δ 7.1-7.45 (m, 4H), 6.88 and 6.82 (d, J = 2.1 Hz, 1H), 6.54 and6.32 (bs, 1H), 4.59 and 4.40 (d, J = 6.3 Hz, 2H), 4.03 and 3.88 (s, 3H),2.51 and 2.35 (s, 3H). 12-005 δ 6.85-7.55 (m, 6H), 5.15-5.3 and 4.9-5.05(m, 1H). 4.4-4.55 and 4.3-4.4 (m, 1H), 2.54 and 2.48 (s, 3H), 1.56 and1.42 (d, J = 6.9 Hz, 3H), 1.15-1.4 (m, 6H). 12-006 δ 7.1-7.45 (m, 8H),6.87 and 6.83 (d, J = 5.1 Hz, 1H), 6.63 and 6.56 (d, J = 7.5 Hz, 1H),5.25-5.35 and 4.95-5.05 (m, 1H), 5.19 and 5.03 (s, 2H), 2.44 and 2.36(s, 3H), 1.55 and 1.40 (d, J = 6.9 Hz, 3H). 12-007 δ 8.77 (s, 1H), 8.00(s, 1H), 7.24 (d, J = 5.1 Hz, 1H), 6.85 (d, J = 5.1 Hz, 1H), 6.66 (bs,1H), 4.73 (d, J = 6.0 Hz, 2H), 4.45-4.6 (m, 1H), 2.44 (s, 3H), 1.36 (t,J = 6.3 Hz, 6H). 12-008 δ 8.51 and 8.48 (d, J = 2.0 Hz, 1H), 7.78 and7.77 (d, J = 2.0 Hz, 1H), 7.83 and 7.70 (bs, 1H), 7.45 and 7.42 (d, J =5.3 Hz, 1H), 7.04 and 6.99 (d, J = 5.3 Hz, 1H), 4.78 and 4.55 (d, J =6.1 and 4.9 Hz, 2H), 4.34 and 4.17 (q, J = 7.0 Hz, 2H), 1.38 and 1.25(t, J = 7.0 Hz, 3H). 12-009 δ 8.50 and 8.48 (d, J = 2.0 Hz, 1H), 7.78and 7.77 (d, J = 2.0 Hz, 1H), 7.58 and 7.44 (bs, 1H), 7.39 and 7.36 (d,J = 5.1 Hz, 1H), 7.14 and 7.10 (d, J = 5.1 Hz, 1H), 4.78 and 4.55 (d, J= 5.8 and 5.1 Hz, 2H), 4.34 and 4.17 (q, J = 7.0 Hz, 2H), 1.38 and 1.25(t, J = 7.0 Hz, 3H). 12-010 δ 8.50 and 8.47 (d, J = 2.4 Hz, 1H), 7.78and 7.76 (d, J = 2.4 Hz, 1H), 7.27 and 7.24 (d, J = 5.1 Hz, 1H), 6.87and 6.84 (d, J = 5.1 Hz, 1H), 6.60 (bs, 1H), 4.70 and 4.49 (d, J = 6.3Hz, 2H), 4.32 and 4.15 (q, J = 7.2 Hz, 2H), 2.51 and 2.46 (s, 3H), 1.37and 1.24 (t, J = 7.2 Hz, 3H). 12-011 δ 8.50 and 8.46 (d, J = 2.0 Hz,1H), 7.79 and 7.77 (d, J = 2.0 Hz, 1H), 7.46 (d, J = 5.1 Hz, 1H), 7.26(d, J = 5.1 Hz, 1H), 7.04 (bs, 1H), 4.74 and 4.51 (d, J = 6.1 and 4.8Hz, 2H), 4.32 and 4.16 (q, J = 7.2 Hz, 2H), 1.37 and 1.24 (t, J = 7.2Hz, 3H). 12-012 δ 8.49 and 8.47 (d, J = 2.1 Hz, 1H), 7.78 and 7.76 (d, J= 2.1 Hz, 1H), 7.27 and 7.23 (d, J = 4.8 Hz, 1H), 6.87 and 6.84 (d, J =4.8 Hz, 1H), 6.58 (bs, 1H), 4.70 and 4.50 (d, J = 5.7 Hz, 2H), 4.07 and3.90 (s, 3H), 2.50 and 2.41 (s, 3H). 12-013 δ 8.50 and 8.48 (d, J = 2.1Hz, 1H), 7.79 and 7.77 (d, J = 2.1 Hz, 1H), 7.2-7.3 (m, 1H), 6.8-6.9 (m,1H), 6.61 (bs, 1H), 4.72 and 4.50 (d, J = 5.4 Hz, 2H), 4.23 and 4.06 (t,J = 6.9 Hz, 2H), 2.53 and 2.43 (s, 3H), 1.55-1.9 (m, 2H), 1.00 and 0.88(t, J = 7.2 Hz, 3H). 12-014 δ 8.48 (d, J = 2.1 Hz, 1H), 7.79 (d, J = 2.1Hz, 1H), 7.24 (d, J = 5.1 Hz, 1H), 6.85 (d, J = 5.1 Hz, 1H), 6.66 (bs,1H), 4.65-4.75 (m, 2H), 4.25-4.4 (m, 1H), 2.44 (s, 3H), 1.5-1.9 (m, 2H),1.33 (d, J = 4.8 Hz, 3H), 0.98 (t, J = 7.5 Hz, 3H). 12-016 δ 8.50 (d, J= 2.1 Hz, 1H), 7.76 (d, J = 2.1 Hz, 1H), 7.29 (d, J = 5.1 Hz, 1H), 6.89(d, J = 5.1 Hz, 1H), 6.76 (bs, 1H), 4.90 (d, J = 4.8 Hz, 2H), 2.54 (s,3H, 1.27 (s, 9H). 12-017 δ 8.51 and 8.49 (d, J = 2.1 Hz, 1H), 7.75-7.85(m, 1H), 7.2-7.35 (m, 1H), 6.8-6.95 (m, 1H), 6.47 (bs, 1H), 4.35-4.8 (m,4H), 2.50 and 2.42 (s, 3H). 12-018 δ 8.51 (d, J = 2.1 Hz, 1H), 7.78 (d,J = 2.1 Hz, 1H), 7.45 (d, J = 5.7 Hz, 1H), 7.36 (bs, 1H), 7.26 (d, J =5.7 Hz, 1H), 5.1-5.3 (m, 1H), 4.05 (t, J = 6.6 Hz, 2H), 15-1.75 (m, 2H),1.43 (d, J = 6.6 Hz, 3H), 0.87 (t, J = 7.2 Hz, 3H). 12-020 δ 8.79 (bs,1H), 7.99 (bs, 1H), 7.45 (d, J = 5.4 Hz, 1H), 7.26 (d, J = 5.4 Hz, 1H),7.01 (bs, 1H), 4.54 (d, J = 4.8 Hz, 2H), 4.07 (t, J = 6.9 Hz, 2H),1.55-1.75 (m, 2H), 0.87 (t, J = 7.5 Hz, 3H). 13-001 δ 8.51 and 8.48 (d,J = 2.1 Hz, 1H), 7.79 and 7.78 (d, J = 2.1 Hz, 1H), 7.35-7.45 (m, 1H),7.05-7.2 (m, 1H), 6.94 and 6.88 (bs, 1H), 4.75 and 4.52 (d, J = 5.4 Hz,2H), 4.33 and 4.15 (q, J = 7.2 Hz, 2H), 1.38 and 1.24 (t, J = 7.2 Hz,3H). 13-002 δ 8.45-8.55 (m, 1H), 7.75-7.9 (m, 1H), 7.2-7.5 (m, 2H), 6.74(bs, 1H), 4.7-4.8 and 4.45-4.55 (m, 2H), 4.25-4.4 and 4.05-4.2 (m, 2H),1.15-1.4 (m, 3H). 13-003 δ 8.51 (d, J = 2.1 Hz, 1H), 7.78 (d, J = 2.1Hz, 1H), 7.43 (d, J = 5.7 Hz, 1H), 7.1-7.25 (m, 2H), 5.15-5.3 (m, 1H),4.05 (t, J = 6.9 Hz, 2H), 1.55-1.75 (m, 2H), 4.47 (d, J = 6.9 Hz, 3H),0.87 (t, J = 7.5 Hz, 3H). 14-001 δ 8.50 and 8.47 (d, J = 1.5 Hz, 1H),7.65-7.8 (m, 2H), 7.48 and 7.44 (d, J = 3.6 Hz, 1H), 6.96 and 6.91 (bs,1H), 4.29 and 4.13 (d, J = 6.0 Hz, 2H), 4.33 and 4.16 (q, J = 7.2 Hz,2H), 1.37 and 1.23 (t, J = 7.2 Hz, 3H). 15-001 δ 8.50 (d, J = 2.0 Hz,1H), 7.76 (d, J = 2.0 Hz, 1H), 7.24 (d, J = 2.7 Hz, 1H), 6.93 (d, J =2.7 Hz, 1H), 6.78 (bs, 1H), 4.49 (d, J = 4.8 Hz, 2H), 4.17 (q, J = 7.0Hz, 2H), 3.68 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H). 15-002 δ 8.48 (d, J =2.1 Hz, 1H), 7.74 (d, J = 2.1 Hz, 1H), 7.24 (bs, 1H), 6.92 (bs, 1H),6.82 (bs, 1H), 4.47 (d, J = 4.8 Hz, 2H), 4.3-4.45 (m, 1H), 3.67 (s, 3H),1.20 (d, J = 6.0 Hz, 6H). 17-001 δ 8.50 and 8.47 (d, J = 2.0 and 2.4 Hz,1H), 7.78 and 7.77 (d, J = 2.4 and 2.0 Hz, 1H), 7.21 and 7.12 (bs, 1H),4.73 and 4.50 (d, J = 6.1 and 4.8 Hz, 2H), 4.32 and 4.15 (q, J = 7.0 Hz,2H), 3.84 and 3.81 (s, 3H), 1.37 and 1.24 (t, J = 7.0 Hz, 3H). 17-002 δ7.98 and 7.80 (s, 1H), 7.1-7.45 (m, 3H), 7.00 and 6.90 (bs, 1H), 6.86and 6.72 (t, J = 54.0 Hz, 1H), 4.59 and 4.40 (d, J = 6.0 Hz, 2H), 4.02and 3.87 (s, 3H), 3.91 and 3.87 (s, 3H). 17-003 δ 7.90 and 7.88 (s, 1H),7.44 and 7.41 (d, J = 1.9 Hz, 1H), 7.1-7.35 (m, 2H), 7.10 (bs, 1H), 6.87and 6.75 (t, J = 54.2 Hz, 1H), 5.2-5.4 and 4.9-5.1 (m, 1H), 4.01 and3.86 (s, 3H), 3.93 and 3.90 (s, 3H), 1.56 and 1.41 (d, J = 7.2 Hz, 3H).17-005 δ 7.92 and 7.82 (s, 1H), 7.2-7.45 (m, 3H), 6.88 and 6.68 (bs,1H), 4.57 and 4.38 (d, J = 6.3 Hz, 2H), 4.03 and 3.87 (s, 3H), 3.95 and3.91 (s, 3H). 17-006 δ 8.50 and 8.47 (d, J = 2.2 Hz, 1H), 7.94 and 7.89(s, 1H), 7.78 and 7.77 (d, J = 2.2 Hz, 1H), 6.9-6.95 and 6.8-6.85 (m,1H), 4.71 and 4.48 (d, J = 5.8 Hz, 2H), 4.32 and 4.16 (q, J = 7.2 Hz,2H), 3.96 and 3.93 (s, 3H), 1.36 and 1.24 (t, J = 7.2 Hz, 3H). 17-008 δ8.49 (d, J = 2.1 Hz, 1H), 7.77 (d, J = 2.1 Hz, 1H), 6.71 (bs, 1H), 4.47(d, J = 4.8 Hz, 2H), 3.89 (s, 3H), 3.84 (s, 3H). 17-011 δ 8.48 (d, J =1.8 Hz, 1H), 7.89 (s, 1H), 7.74 (d, J = 1.8 Hz, 1H), 7.05 (bs, 1H), 6.83(t, J = 54.6 Hz, 1H), 4.48 (d, J = 5.1 Hz, 2H), 4.3-4.45 (m, 1H), 3.92(s, 3H), 1.20 (d, J = 6.3 Hz, 6H). 17-012 δ 8.79 (bs, 1H), 7.97 (bs,1H), 7.90 (s, 1H), 7.00 (bs, 1H), 6.82 (t, J = 54.3 Hz, 1H), 4.52 (d, J= 5.1 Hz, 2H), 4.07 (t, J = 6.6 Hz, 2H), 3.92 (s, 3H), 1.55-1.75 (m,2H), 0.87 (t, J = 7.5 Hz, 3H). 18-001 δ 8.49 (d, J = 2.0 Hz, 1H), 7.76(d, J = 2.0 Hz, 1H), 7.61 (bs, 1H), 4.48 (d, J = 5.5 Hz, 2H), 4.16 (q, J= 7.0 Hz, 2H), 2.55 (s, 3H), 1.23 (t, J = 7.0 Hz, 3H). 19-001 δ 8.50 and8.48 (d, J = 2.1 Hz, 1H), 7.80 and 7.78 (d, J = 2.1 Hz, 1H), 6.55 (bs,1H), 4.69 and 4.47 (d, J = 6.3 Hz, 2H), 4.32 and 4.15 (q, J = 7.2 Hz,2H), 2.68 and 2.65 (s, 3H), 2.65 and 2.57 (s, 3H), 1.37 and 1.24 (t, J =7.2 Hz, 3H). 20-001 δ 8.50 and 8.47 (d, J = 2.1 Hz, 1H), 7.79 and 7.77(d, J = 2.1 Hz, 1H), 7.17 and 7.08 (t, J = 54.6 Hz, 1H), 6.8-7.05 (m,1H), 4.70 and 4.47 (d, J = 6.3 Hz, 2H), 4.32 and 4.16 (q, J = 7.2 Hz,2H), 2.75 and 2.72 (s, 3H), 1.37 and 1.24 (t, J = 7.2 Hz, 3H). 20-002 δ7.1-7.5 (m, 4H), 5.1-5.25 and 4.85-5.0 (m, 1H), 4.26 and 4.11 (q, J =7.2 Hz, 2H), 2.74 and 2.73 (s, 3H), 1.4-1.6 (m, 3H), 1.34 and 1.21 (t, J= 7.2 Hz, 3H). 20-003 δ 8.50 and 8.46 (d, J = 2.1 Hz, 1H), 7.80 and 7.78(d, J = 2.1 Hz, 1H), 6.95-7.1 (m, 1H), 4.72 and 4.48 (d, J = 5.7 Hz,2H), 4.32 and 4.15 (q, J = 7.2 Hz, 2H), 2.73 and 2.71 (s, 3H), 1.36 and1.24 (t, J = 7.2 Hz, 3H). 20-004 δ 8.47 (d, J = 2.0 Hz, 1H), 7.81 (d, J= 2.0 Hz, 1H), 7.04 (bs, 1H), 4.75 (d, J = 5.8 Hz, 2H), 4.09 (d, J = 7.2Hz, 2H), 2.71 (s, 3H), 1.0-1.3 (m, 1H), 0.4-0.65 (m, 2H), 0.15-0.4 (m,2H). 20-005 δ 8.50 and 8.43 (d, J = 2.0 Hz, 1H), 7.80 and 7.76 (d, J =2.0 Hz, 1H), 7.15-7.45 (m, 5H), 6.95 (bs, 1H), 5.41 and 5.26 (q, J = 6.8Hz, 1H), 4.45 and 4.33 (d, J = 4.9 and 5.8 Hz, 2H), 2.73 and 2.71 (s,3H), 1.67 and 1.48 (d, J = 6.8 Hz, 3H). 21-001 δ 8.49 (d, J = 2.0 Hz,1H), 7.76 (d, J = 2.0 Hz, 1H), 7.35 (bs, 1H), 4.51 (d, J = 5.1 Hz, 2H),4.28 (s, 3H), 4.17 (q, J = 7.0 Hz, 2H), 1.23 (t, J = 7.0 Hz, 3H). 22-001δ 7.43 and 7.42 (d, J = 1.8 Hz, 1H), 7.25-7.35 (m, 1H), 7.12 and 7.10(s, 1H), 6.74 and 6.65 (bs, 1H), 5.05-5.15 and 4.8-4.9 (m, 1H),4.05-4.45 (m, 4H), 3.05-3.15 (m, 2H), 1.15-1.65 (m, 6H). 22-002 δ 8.50and 8.47 (d, J = 2.1 Hz, 1H), 7.79 and 7.77 (d, J = 2.1 Hz, 1H), 6.49(bs, 1H), 4.1-4.65 (m, 6H), 3.0-3.15 (m, 2H), 1.35 and 1.23 (t, J = 7.2Hz, 3H). 22-003 δ 8.49 and 8.46 (d, J = 2.1 Hz, 1H), 7.79 and 7.76 (d, J= 2.1 Hz, 1H), 6.49 (bs, 1H), 4.3-4.65 (m, 5H), 3.0-3.15 (m, 2H), 1.33and 1.20 (d, J = 6.3 Hz, 6H). 23-004 δ 8.35-8.4 (m, 1H), 7.0-7.85 (m,9H), 6.31 (bs, 1H), 5.22 and 5.06 (s, 2H), 4.65 and 4.76 (d, J = 6.0 Hz,2H). 24-001 δ 8.55 and 8.50 (s, 1H), 7.4-7.75 (m, 4H), 6.42 (bs, 1H),4.35-4.8 (m, 3H), 1.35 and 1.21 (d, J = 6.3 Hz, 6H). 26-001 δ 6.65-7.75(m, 7H), 5.35-5.5 and 5.05-5.2 (m, 1H). 4.23 and 4.12 (q, J = 7.2 Hz,2H), 1.59 and 1.41 (d, J = 7.2 Hz, 3H), 1.30 and 1.22 (t, J = 7.2 Hz,3H). 26-002 δ 6.5-7.75 (m, 12H), 4.8-5.55 (m, 2H), 1.3-1.7 (m, 6H).26-003 δ 6.55-7.75 (m, 6H), 5.2-5.45 and 5.0-5.15 (m, 1H), 4.05-4.35 (m,2H), 1.2-1.65 (m, 6H). 27-001 δ 7.45-7.7 (m, 5H), 5.95-6.1 (m, 1H),4.8-4.9 (m, 1H), 4.02 (s, 3H), 3.60 (s, 3H), 1.51 (d, J = 6.9 Hz, 3H),1.35 (d, J = 6.0 Hz, 6H). 27-002 δ 7. 5-7.75 (m, 4H), 6.97 (d, J = 7.8Hz, 1H), 5.15-5.25 (m, 1H), 4.75-4.9 (m, 1H), 3.90 (s, 3H), 3.64 (s,3H). 1.40 (d, J = 7.2 Hz, 3H), 1.37 (d, J = 6.6 Hz, 6H). 29-001 δ7.4-7.85 (m, 4H), 6.58 and 6.41 (bs, 1H), 4.85 and 4.73 (d, J = 5.7 Hz,2H), 4.05 and 4.03 (s, 3H). 29-002 δ 7.4-7.8 (m, 4H), 6.61 and 6.42 (bs,1H), 4.87 and 4.74 (d, J = 5.4 Hz, 2H), 4.2-4.4 (m, 2H), 1.25-1.4 (m,3H). 30-007 δ 6.5-8.65 (m, 13H), 4.85-5.85 (m, 1H), 1.4-1.7 (m, 3H).30-009 δ 6.95-7.75 (m, 6H), 6.3-6.7 (m, 1H), 5.0-5.3 (m, 1H), 1.4-1.65(m, 3H). 30-010 δ 8.18 and 8.08 (d, J = 2.4 Hz, 1H), 8.32 (bs, 1H),7.3-7.75 (m, 5H), 6.45 (bs, 1H), 4.69 and 4.54 (d, J = 6.3 and 5.3 Hz,2H). 30-012 δ 8.47 and 8.42 (d, J = 2.0 Hz, 1H), 8.20 (bs, 1H), 7.4-7.75(m, 5H), 6.64 (bs, 1H), 4.90 and 4.65 (d, J = 6.3 and 5.3 Hz, 2H).30-013 δ 7.15-7.75 (m, 7H), 6.55 (bs, 1H), 5.35-5.5 and 5.05-5.2 (m,1H), 1.4-1.7(m, 3H). 30-014 δ 7.1-7.75 (m, 6H), 6.44 (bs, 1H), 5.05-5.25(m, 1H), 1.4-1.5 (m, 3H). 30-016 δ 7.15-8.05 (m, 8H), 6.90 and 6.59 (bs,1H), 5.25-5.4 and 5.0-5.1 (m, 1H), 1.63 and 1.46 (d, J = 6.9 Hz, 3H).30-018 δ 8.51 and 8.41 (d, J = 2.4 Hz, 1H), 7.92 and 7.81 (bs, 1H),7.4-7.75 (m, 4H), 7.00 and 6.77 (d, J = 7.8 Hz, 1H), 5.75-5.9 and5.2-5.35 (m, 1H), 1.59 and 1.44 (d, J = 6.9 Hz, 3H). 30-019 δ 7.94 and7.91 (s, 1H), 7.4-7.75 (m, 4H), 6.45 and 6.39 (bs, 1H), 4.75 and 4.54(d, J = 6.3 Hz, 2H). 30-020 δ 7.4-7.85 (m, 5H), 6.47 (bs, 1H), 4.83 and4.56 (d, J = 6.0 Hz, 2H), 4.02 and 3.99 (s, 3H). 30-021 δ 7.1-7.75 (m,8H), 6.85 and 6.55 (bs, 1H), 5.2-5.4 and 5.0-5.2 (m, 1H), 1.64 and 1.47(d, J = 6.9 Hz, 3H). 30-024 δ 8.80 and 8.75 (d, J = 1.7 Hz, 1H), 8.09(d, J = 1.7 Hz, 1H), 7.45-7.75 (m, 4H), 6.61 (bs, 1H), 5.78 (bs, 1H),4.86 and 4.59 (d, J = 6.3 and 5.1 Hz, 2H), 4.04 and 4.03 (s, 3H), 2.23and 2.22 (s, 3H). 30-025 δ 8.81 and 8.74 (d, J = 1.8 Hz, 1H), 8.06 and8.05 (d, J = 1.8 Hz, 1H), 7.35-7.8 (m, 4H), 6.47 and 6.39 (bs, 1H), 4.83(d, J = 6.0 Hz, 1H), 4.59 (d, J = 6.0 Hz, 1H). 30-028 δ 9.04 (d, J = 1.7Hz, 1H), 8.31 (d, J = 1.7 Hz, 1H), 7.35-7.75 (m, 4H), 6.48 (bs, 1H),4.48 (d, J = 6.1 Hz, 2H). 31-001 δ 8.43 (d, J = 2.4 Hz, 1H), 7.4-7.8 (m,5H), 6.37 (bs, 1H), 5.99 (dd, J = 8.5, 4.6 Hz, 1H), 4.1-4.35 (m, 2H).31-002 δ 8.43 (d, J = 1.2 Hz, 1H), 7.4-7.75 (m, 5H), 6.55 (bs, 1H), 6.21(t, J = 6.3 Hz, 1H), 4.40 (t, J = 6.3 Hz, 2H). 31-004 δ 7.99 (d, J = 7.2Hz, 1H), 7.4-7.75 (m, 4H), 6.46 (bs, 1H), 6.30 (dd, J = 6.6, 5.8 Hz,1H), 4.3-4.4 (m, 2H). 31-005 δ 7.77 (s, 1H), 7.45-7.75 (m, 4H), 6.48(bs, 1H), 6.2-6.3 (m, 1H), 4.2-4.45 (m, 2H), 3.96 (s, 3H). 31-008 δ 8.75(d, J = 1.8 Hz, 1H), 8.09 (d, J = 1.8 Hz, 1H), 7.45-7.75 (m, 4H), 6.57(bs, 1H), 6.38 (dd, J = 7.4, 5.0 Hz, 1H), 4.3-4.6 (m, 2H), 4.04 (s, 3H),2.22 (s, 3H). 31-009 δ 8.77 (d, J = 1.8 Hz, 1H), 8.12 (d, J = 1.8 Hz,1H), 7.45-7.75 (m, 4H), 6.49 (t, J = 6.3 Hz, 1H), 6.43 (t, J = 6.3 Hz,1H), 4.40 (t, J = 6.3 Hz, 2H). 31-010 δ 9.07 (d, J = 1.4 Hz, 1H), 8.35(d, J = 1.4 Hz, 1H), 7.4-7.8 (m, 4H), 6.54 (dd, J = 6.9, 5.8 Hz, 1H),6.29 (dd, J = 7.2, 4.7 Hz, 1H), 4.45 (ddd, J = 14.9, 6.9, 4.7 Hz, 1H),4.38 (ddd, J = 14.9, 7.2, 5.8 Hz, 1H). 32-004 δ 7.9-8.0 (m, 1H),7.5-7.75 (m, 7H), 7.00 (bs, 1H), 5.65-5.8 (m, 1H), 1.56 (d, J = 7.2 Hz,3H), 1.36 (s, 9H). 32-011 δ 8.33 (s, 1H), 8.19 (s, 1H), 8.02 (s, 1H),7.5-7.8 (m, 4H), 6.77 (bs, 1H), 5.65-5.8 (m, 1H), 1.56 (d, J = 7.2 Hz,3H). 32-012 δ 7.1-7.75 (m, 8H), 6.96 (bs, 1H), 5.65-5.8 (m, 1H),4.55-4.7 (m, 1H), 1.56 (d, J = 7.2 Hz, 3H), 1.37 (d, J = 6.0 Hz, 6H).32-013 δ 7.5-8.6 (m, 11H), 6.6-7.1 (m, 1H), 4.9-6.0 (m, 1H), 1.45-1.65(m, 3H). 32-015 δ 7.0-7.9 (m, 6H), 6.81 (bs, 1H), 5.5-5.65 (m, 1H),1.5-1.6 (m, 3H). 32-018 δ 7.15-7.75 (m, 6H), 6.68 (bs, 1H), 5.25-5.4 (m,1H), 1.50 (d, J = 7.2 Hz, 3H). 32-019 δ 7.45-7.75 (m, 6H), 6.7-6.9 (m,1H), 5.45-5.6 (m, 1H), 1.5-1.6 (m, 3H). 32-024 δ 7.85-7.9 (m, 1H),7.5-7.75 (m, 6H), 6.88 (bs, 1H), 5.5-5.65 (m, 1H), 1.49 (d, J = 7.2 Hz,3H). 32-025 δ 7.5-7.75 (m, 5H), 7.2-7.3 (m, 1H), 7.05-7.15 (m, 1H), 6.35(bs, 1H), 5.5-5.65 (m, 1H), 1.46 (d, J = 7.2 Hz, 3H). 32-029 δ 7.5-7.8(m, 7H), 6.71 (bs, 1H), 5.45-5.6 (m, 1H), 1.46 (d, J = 7.5 Hz, 3H).32-030 δ 7.65-7.75 (m, 1H), 7.5-7.65 (m, 4H), 7.25-7.35 (m, 1H),7.15-7.2 (m, 1H), 6.82 (bs, 1H), 5.55-5.7 (m, 1H), 2.40 (s, 3H), 1.45(d, J = 7.2 Hz, 3H). 32-031 δ 7.45-7.8 (m, 7H), 6.65 (bs, 1H), 5.45-5.6(m, 1H), 1.49 (d, J = 7.8 Hz, 3H). 32-032 δ 8.86 (s, 1H), 8.11 (s, 1H),7.45-7.8 (m, 4H), 5.13 (bs, 1H), 5.12 (d, J = 4.8 Hz, 2H). 32-033 δ7.65-7.75 (m, 2H), 7.5-7.65 (m, 3H), 7.00 (d, J = 2.4 Hz, 1H), 6.75-6.95(m, 2H), 5.6-5.75 (m, 1H), 3.87 (s, 3H), 1.46 (d, J = 7.2 Hz, 3H).32-034 δ 6.7-7.85 (m, 8H), 5.5-5.7 (m, 1H), 2.52 (s, 3H), 1.45 (d, J =7.2 Hz, 3H). 32-035 δ 7.45-7.8 (m, 7H), 6.59 (bs, 1H), 5.35-5.5 (m, 1H),1.49 (d, J = 7.2 Hz, 3H). 32-037 δ 8.07 (d, J = 1.5 Hz, 1H), 7.9-7.95(m, 1H), 7.7-7.75 (m, 1H), 7.5-7.65 (m, 4H), 6.73 (bs, 1H), 5.5-5.65 (m,1H), 4.15 (s, 2H), 1.46 (d, J = 7.2 Hz, 3H), 1.40 (s, 6H). 32-038 δ7.65-7.75 (m, 1H), 7.45-7.65 (m, 5H), 7.35-7.45 (m, 1H), 6.78 (bs, 1H),6.69 (dd, J = 17.7, 11.1 Hz, 1H), 5.88 (d, J = 17.7 Hz, 1H), 5.55-5.7(m, 1H), 5.50 (d, J = 11.1 Hz, 1H), 1.47 (d, J = 7.2 Hz, 3H). 32-039 δ7.4-7.75 (m, 7H), 6.72 (bs, 1H), 5.5-5.65 (m, 1H), 1.45 (d, J = 7.2 Hz,3H), 0.27 (s, 9H). 32-040 δ 7.35-7.8 (m, 12H), 6.83 (bs, 1H), 5.6-5.75(m, 1H), 1.51 (d, J = 7.2 Hz, 3H). 32-041 δ 7.3-7.8 (m, 11H), 6.80 (bs,1H), 5.6-5.75 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H). 32-042 δ 7.78 (d, J =8.7 Hz, 1H), 7.5-7.75 (m, 5H), 7.39 (dd, J = 8.7, 2.1 Hz, 1H), 7.13 (t,J = 2.1 Hz, 2H), 6.79 (bs, 1H), 6.40 (t, J = 2.1 Hz, 2H), 5.6-5.75 (m,1H), 1.50 (d, J = 7.2 Hz, 3H). 32-043 δ 7.25-8.05 (m, 8H), 6.87 (bs,1H), 6.5-6.55 (m, 1H), 6.35-6.4 (m, 1H), 5.55-5.7 (m, 1H), 1.48 (d, J =6.9 Hz, 3H). 32-044 δ 8.0-8.1 (m, 1H), 8.95 (d, J = 2.1 Hz, 1H),7.5-7.85 (m, 6H), 6.79 (d, J = 2.1 Hz, 1H), 6.74 (bs, 1H), 5.55-5.7 (m,1H), 1.49 (d, J = 6.9 Hz, 3H). 32-046 δ 7.05-7.75 (m, 7H), 6.70 (bs,1H), 5.45-5.65 (m, 1H), 1.48 (d, J = 6.9 Hz, 3H). 32-047 δ 7.5-7.85 (m,6H), 6.73 (bs, 1H), 5.45-5.6 (m, 1H), 1.5-1.6 (m, 3H). 32-048 δ 7.7-7.75(m, 2H), 7.5-7.65 (m, 3H), 7.3-7.35 (m, 2H), 6.86 (d, J = 7.2 Hz, 1H),5.5-5.65 (m, 1H), 2.49 (s, 3H), 1.44 (d, J = 7.2 Hz, 3H). 32-049 δ7.45-7.95 (m, 7H), 6.60 (bs, 1H), 5.4-5.55 (m, 1H), 1.50 (d, J = 7.2 Hz,3H). 32-051 δ 7.65-7.75 (m, 2H), 7.4-7.65 (m, 5H), 6.77 (bs, 1H), 6.23(s, 1H), 5.45-5.6 (m, 1H), 3.9-4.05 (m, 4H), 1.45 (d, J = 7.2 Hz, 3H).32-052 δ 8.3-8.5 (m, 2H), 7.8-7.95 (m, 2H), 7.5-7.75 (m, 6H), 6.93 (bs,1H), 5.65-5.8 (m, 1H), 1.48 (d, J = 7.2 Hz, 3H). 32-055 δ 8.76 (s, 1H),7.5-7.8 (m, 4H), 6.83 (bs, 1H), 5.08 (d, J = 5.1 Hz, 2H). 32-057 δ 8.69(d, J = 2.1 Hz, 1H), 8.2-8.25 (m, 1H), 7.45-7.75 (m, 4H), 6.69 (bs, 1H),5.9-6.1 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H). 33-001 δ 8.61 (s, 1H),7.5-7.8 (m, 4H), 6, 65 (bs, 1H), 5.05-5.15 (m, 2H). 35-001 δ 6.55-7.75(m, 7H), 5.35-5.5 and 5.1-5.25 (m, 1H), 1.63 and 1.43 (d, J = 7.2 Hz,3H). 36-002 δ 7.5-7.75 (m, 5H), 6.78 (bs, 1H), 5.75-5.95 and 5.45-5.65(m, 1H), 1.45-1.65 (m, 3H). 37-001 δ 8.94 (bs, 2H), 7.45 (d, J = 1.8 Hz,1H), 7.34 (dd, J = 8.1, 1.8 Hz, 1H), 7.23 (d, J = 8.1 Hz, 1H), 4.52 (q,J = 6.9 Hz, 1H). 4.16 (q, J = 6.9 Hz, 2H), 1.60 (d, J = 6.9 Hz, 3H),1.23 (t, J = 6.9 Hz, 3H). 37-008 δ 8.50 (d, J = 2.1 Hz, 1H), 7.76 (d, J= 2.1 Hz, 1H), 4.35 (sep, J = 6.1 Hz, 1H), 3.73 (s, 2H), 1.18 (d, J =6.1 Hz, 6H). 37-009 δ 8.98 (bs, 1H), 8.5-8.6 (m, 1H), 7.75-7.85 (m, 1H),4.35-4.6 (m, 2H), 1.2-1.75 (m, 9H). 37-011 δ 8.51 and 8.48 (d, J = 2.0Hz, 1H), 7.79 and 7.77 (d, J = 2.0 Hz, 1H), 4.04 and 3.89 (d, J = 7.2Hz, 2H), 3.95 and 3.76 (s, 2H), 2.33 (bs, 2H), 0.95-1.3 (m, 1H),0.4-0.65 (m, 2H), 0.05-0.4 (m, 2H). 37-015 δ 8.51 and 8.44 (d, J = 2.0Hz, 1H), 7.77 and 7.74 (d, J = 2.0 Hz, 1H), 7.1-7.4 (m, 5H), 5.37 and5.24 (q, J = 6.8 Hz, 1H), 3.96 and 3.70 (s, 2H), 2.15 (bs, 2H), 1.64 and1.46 (d, J = 6.8 Hz, 3H). 37-016 δ 8.87 (bs, 3H), 8.45-8.5 (m, 1H),7.7-7.75 (m, 1H), 6.9-7.45 (m, 4H), 5.42 and 5.32 (q, J = 6.9 Hz, 1H),4.25 and 4.02 (bs, 2H), 1.70 and 1.53 (d, J = 6.9 Hz, 3H). 37-019 δ 8.47and 8.46 (d, J = 1.7 Hz, 1H), 7.77 and 7.74 (d, J = 1.7 Hz, 1H), 4.48(s, 2H), 4.48 and 4.35 (sep, J = 6.3 Hz, 1H), 3.89 and 3.73 (s, 2H),3.43 and 3.33 (s, 3H), 1.32 and 1.18 (d, J = 6.3 Hz, 6H). 37-020 δ 8.24and 8.23 (d, J = 2.5 Hz, 1H), 7.27 and 7.26 (d, J = 2.5 Hz, 1H), 4.46and 4.34 (sep, J = 6.3 Hz, 1H), 3.89 and 3.88 (s, 3H), 3.87 and 3.72 (s,2H), 1.31 and 1.19 (d, J = 6.3 Hz, 6H). 37-024 δ 8.97 (bs, 3H), 8.53 (d,J = 2.1 Hz, 1H), 7.77 (d, J = 2.1 Hz, 1H), 4.52 (bs, 1H), 4.11 (t, J =6.9 Hz, 2H), 1.55-1.75 (m, 5H), 0.86 (t, J = 7.5 Hz, 3H). 37-025 δ 8.79(d, J = 1.5 Hz, 1H), 8.01 (d, J = 1.5 Hz, 1H), 4.06 (s, 3H), 3.94 (s,2H), 1.61 (bs, 2H). 37-026 δ 8.77 (d, J = 1.5 Hz, 1H), 8.00 (d, J = 1.5Hz, 1H), 4.19 (t, J = 6.9 Hz, 2H), 3.94 (s, 2H), 1.75 (sxt, J = 6.9 Hz,2H), 1.64 (bs, 2H), 0.99 (t, J = 6.9 Hz, 3H). 37-027 δ 8.77 (d, J = 1.5Hz, 1H), 8.01 (d, J = 1.5 Hz, 1H), 4.49 (sep, J = 6.3 Hz, 1H), 3.92 (s,2H), 1.73 (bs, 2H), 1.33 (d, J = 6.9 Hz, 6H). 38-004 δ 8.35 and 8.20(bs, 1H), 7.6-7.85 (m, 5H), 5.75-5.9 and 5.1-5.35 (m, 1H), 4.02 and 3.85(bs, 3H), 2.05-2.6 (m, 2H), 0.85-1.05 (m, 3H). 38-009 δ 8.70 and 8.49(bs, 1H), 7.94 and 7.92 (bs, 1H), 7.65-7.85 (m, 4H), 6.10 and 5.53 (q, J= 7.2 Hz, 1H), 1.85 and 1.80 (d, J = 7.2 Hz, 3H). 38-012 δ 8.63 and 8.45(d, J = 1.7 Hz, 1H), 8.61 and 8.29 (d, J = 1.7 Hz, 1H), 7.6-7.9 (m, 4H),5.08 and 4.81 (s, 2H), 4.48 and 4.40 (s, 2H), 3.45 and 3.35 (s, 3H).38-013 δ 8.41 and 8.28 (d, J = 1.8 Hz, 1H), 7.6-7.9 (m, 5H), 5.00 and4.78 (s, 2H), 4.46 and 4.39 (s, 2H), 4.46 and 4.32 (sep, J = 6.3 Hz,1H), 3.43 and 3.33 (s, 3H), 1.25 and 1.12 (d, J = 6.3 Hz, 6H). 38-014 δ8.22 and 8.04 (d, J = 2.4 Hz, 1H), 7.6-7.9 (m, 4H), 7.23 and 7.20 (d, J= 2.4 Hz, 1H), 5.07 and 4.79 (s, 2H), 3.86 and 3.80 (s, 3H). 38-016 δ8.18 and 8.03 (d, J = 2.5 Hz, 1H), 7.6-7.9 (m, 4H), 7.21 and 7.18 (d, J= 2.5 Hz, 1H), 4.97 and 4.76 (s, 2H), 4.45 and 4.32 (sep, J = 6.3 Hz,1H), 3.85 and 3.79 (s, 3H), 1.25 and 1.12 (d, J = 6.3 Hz, 6H). 39-010 δ8.66 (bs, 1H), 8.03 (bs, 1H), 7.8-7.85 (m, 2H), 7.65-7.75 (m, 2H), 5.89(q, J = 7.2 Hz, 1H), 1.70 (d, J = 7.2 Hz, 3H). 39-011 δ 8.55 (d, J = 1.2Hz, 1H), 7.85-7.95 (m, 2H), 7.83 (d, J = 1.2 Hz, 1H), 7.7-7.8 (m, 2H),5.34 (s, 2H), 4.56 (s, 2H), 3.48 (s, 3H). 40-001 δ 8.75 (bs, 2H), 8.39(d, J = 2.1 Hz, 1H), 7.83 (d, J = 2.1 Hz, 1H), 5.83 (q, J = 7.5 Hz, 1H),1.57 (d, J = 7.5 Hz, 3H). 40-002 δ 8.75 (bs, 2H), 8.69 (s, 1H), 8.05 (s,1H), 5.75-5.9 (m, 1H), 1.59 (d, J = 6.9 Hz, 3H). 41-001 δ 7.1-7.5 (m,3H), 5.03 (bs, 1H), 4.64 (bs, 1H), 1.41 (s, 9H), 1.3-1.4 (m, 3H). 41-004δ 8.49 and 8.47 (d, J = 2.1 Hz, 1H), 7.77 and 7.75 (d, J = 2.1 Hz, 1H),5.01 (bs, 1H), 4.39 and 4.20 (d, J = 5.4 Hz, 2H), 4.03 and 3.86 (s, 3H),1.38 and 1.34 (s, 9H). 41-005 δ 8.50 (d, J = 2.1 Hz, 1H), 7.75 (d, J =2.1 Hz, 1H), 5.14 (bs, 1H), 4.76 (bs, 1H), 4.01 and 3.86 (s, 3H),1.3-1.55 (m, 12H). 41-008 δ 8.45-8.65 (m, 1H), 7, 7-7.9 (m, 1H),4.05-4.3 (m, 2H), 0.85-1.5 (m, 21H). 41-009 δ 8.50 and 8.47 (d, J = 2.1Hz, 1H), 7.78 and 7.75 (d, J = 2.1 Hz, 1H), 5.02 (bs, 1H), 3.95-4.45 (m,4H), 1.4-1.85 (m, 2H), 1.39 and 1.35 (s, 9H), 0.98 and 0.86 (t, J = 7.5Hz, 3H). 41-010 δ 8.49 and 8.46 (d, J = 2.4 Hz, 1H), 7.77 and 7.74 (d, J= 2.4 Hz, 1H), 5.01 (bs, 1H), 4.1-4.55 (m, 3H), 1.39 and 1.35 (s, 9H),1.31 and 1.17 (d, J = 6.3 Hz, 6H). 41-011 δ 8.45-8.6 (m, 1H), 7.7-7.8(m, 1H), 4.25-5.3 (m, 3H), 1.1-1.6 (m, 18H). 41-013 δ 8.49 and 8.46 (d,J = 2.1 Hz, 1H), 7.77 and 7.75 (d, J = 2.1 Hz, 1H), 5.05 (bs, 1H), 4.42and 4.19 (d, J = 6.3 Hz, 2H), 4.03 and 3.88 (d, J = 7.2 Hz, 2H), 1.39and 1.35 (s, 9H), 1.1-1.3 (m, 1H), 0.55-0.65 and 0.45-0.55 (m, 2H),0.3-0.35 and 0.2-0.25 (m, 2H). 41-014 δ 8.48 and 8.46 (d, J = 2.1 Hz,1H), 7.77 and 7.73 (d, J = 2.1 Hz, 1H), 5.03 (bs, 1H), 4.05-4.45 (m,3H), 0.8-1.85 (m, 17H). 41-015 δ 8.4-8.5 (m, 1H), 7.7-7.8 (m, 1H), 5.05(bs, 1H), 4.35-4.45 (m, 2H), 1.3-1.4 (m, 18H). 41-017 δ 8.50 and 8.43(d, J = 2.1 Hz, 1H), 7.76 and 7.72 (d, J = 2.1 Hz, 1H), 7.2-7.4 (m, 5H),5.36 and 5.24 (q, J = 6.6 Hz, 1H), 4.8-5.05 (m, 1H), 4.45 and 4.15 (d, J= 5.4 Hz, 2H), 1.63 and 1.45 (d, J = 6.6 Hz, 3H), 1.36 and 1.35 (s, 9H).41-018 δ 8.50 and 8.44 (d, J = 2.1 Hz, 1H), 7.76 and 7.73 (d, J = 2.1Hz, 1H), 6.9-7.4 (m, 4H), 5.34 and 5.22 (q, J = 6.9 Hz, 1H), 4.97 (bs,1H), 4.4-4.5 and 4.1-4.2 (m, 2H), 1.3-1.65 (m, 12H). 41-019 δ 8.50 (d, J= 2.1 Hz, 1H), 7.75 (d, J = 2.1 Hz, 1H), 5.21 (bs, 1H), 4.75 (bs, 1H),4.02 (t, J = 6.9 Hz, 2H), 1.5-1.7 (m, 2H), 1.41 (s, 9H), 1.36 (d, J =6.9 Hz, 3H), 0.86 (t, J = 7.5 Hz, 3H). 42-001 δ 7.54 (d, J = 7.5 Hz,1H), 7.45-7.5 (m, 1H), 7.3-7.4 (m, 1H), 5.30 (bs, 1H), 4.95-5.1 (m, 1H),1.43 (m, 9H), 1.33 (d, J = 7.2 Hz, 3H). 42-005 δ 8.55 (d, J = 1.8 Hz,1H), 7.83 (d, J = 1.8 Hz, 1H), 5.65 (bs, 1H), 5.37 (bs, 1H), 1.44 (s,9H), 0.91 (s, 9H). 42-006 δ 8.64 (d, J = 2.1 Hz, 1H), 8.21 (d, J = 2.1Hz, 1H), 5.31 (bs, 1H), 4.75 (d, J = 4.5 Hz, 2H), 1.47 (s, 9H).

Test Example

Now, usefulness of the compounds of the present invention as pesticideswill be described in detail by referring to the following Test Examples,but the present invention is by no restricted thereto.

Preparation of Test Solutions a:

Compounds of the present invention were dissolved in a solvent foremulsion (a mixture of Sorpol (registered trademark) 3005XL(manufactured by Toho Chemical Industry Co., Ltd.):N-methylpyrrolidone:Solvesso (registered trademark) 200 (manufactured byExxonMobil Chemical) in a ratio of 1:5:2) to prepare 20% emulsifiableconcentrates. Then, distilled water was added to dilute the emulsifiableconcentrates to the predetermined concentration (500 ppm), and theobtained solutions were used in the following Test Examples 1 to 7.

Preparation of Test Solutions B:

Compounds of the present invention were dissolved in dimethylsulfoxideto prepare 1% solutions. Then, distilled water was added to dilute thesolutions to the predetermined concentration (100 ppm), and the obtainedsolutions were used in the following Test Examples 8 to 12.

Test Example 1 Test on the Preventive Effect Against Cucumber PowderyMildew

Cucumber (cultivar: Sagami Hanjiro) was planted in 90 cm³ plastic pots,and in the seed leaf stage, 5 ml per pot of test solutions A of thecompounds of the present invention were spray-inoculated. After dryingin air, the pots were placed in an air-conditioned greenhouse (20° C.),and a suspension of conidium of Erysiphe polygoni (synonym: Erysiphebetae) was sprayed. After the pots were placed at the same temperaturefor 9 days, the proportion of the formed lesion in the inoculated leaveswas measured to calculate the control value in accordance with thefollowing formula. Here, the test was carried out in duplicate.

Control value=[1−(lesion area ratio in treated plot/lesion area ratio innon-treated plot)]×100

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-001 to 1-015, 1-018 to 1-021, 1-023 to 1-025, 1-028 to1-030, 1-032 to 1-034, 1-036 to 1-038, 1-040 to 1-076, 1-078 to 1-102,2-002 to 2-019, 2-020*, 2-021 to 2-081, 2-083 to 2-089, 2-090*, 2-091,2-092, 2-093*, 2-095 to 2-111, 2-113, 2-115, 2-117 to 2-121, 2-123,2-124, 2-126, 2-127, 2-128, 2-129, 2-131 to 2-139, 2-141 to 2-205, 2-207to 2-214, 2-215*, 2-216 to 2-228, 2-230, 2-231, 2-233 to 2-235, 2-237,2-238, 2-240 to 2-251, 3-001, 3-003, 3-004, 3-006, 3-007, 3-010 to3-030, 3-033 to 3-051, 4-002 to 4-006, 4-008 to 4-011, 5-001, 6-001 to6-005, 7-001 to 7-009, 9-001 to 9-006, 10-001, 11-001, 11-002, 12-001,12-003 to 12-017, 13-001, 13-002, 15-001, 17-001, 17-002*, 17-003 to17-006, 17-007*, 17-008 to 17-010, 19-001, 20-001 to 20-003, 20-004*,20-005 to 20-007, 21-001, 22-001 to 22-003, 23-001, 23-002, 23-004,25-001 to 25-004, 26-001 to 26-003, 27-002, 28-001, 30-017, 31-007,32-026, 32-028 and 32-032 of the present invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 2: Test on the preventive effect against cucumbergray mold (spore inoculation)

Cucumber (cultivar: Sagami Hanjiro) was planted in 90 cm³ plastic pots,and in the seed leaf stage, 5 ml per pot of test solutions A of thecompounds of the present invention were applied. After drying in air,the treated leaves were cut and put in plastic containers. 30 μl of amixture of a suspension of conidium of Botrytis cinerea and a dissolvedPDA medium in a ratio of 1:1 was dropped on each treated leaf andinoculated. After the inoculation, the plastic containers were placed at20° C. in humid conditions for 3 days, and the proportion of the formedlesion in the inoculated leaves was measured to calculate the controlvalue in accordance with the same formula as in Test Example 1. Here,the test was carried out in duplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-001, 1-005 to 1-007, 1-009, 1-024, 1-040 to 1-044,1-046, 1-049 to 1-054, 1-057 to 1-060, 1-063, 1-065 to 1-067, 1-070 to1-075, 1-079, 1-082, 1-083, 1-085, 1-090, 1-092, 1-093, 1-096, 1-097,1-099, 1-100, 1-102, 2-002 to 2-019, 2-020*, 2-021 to 2-030, 2-032 to2-034, 2-040 to 2-051, 2-053 to 2-069, 2-071 to 2-086, 2-088, 2-089,2-091, 2-092, 2-096 to 2-101, 2-104, 2-105, 2-107, 2-111, 2-114*, 2-115,2-117, 2-118, 2-120, 2-121, 2-123, 2-124, 2-126 to 2-129, 2-131 to2-144, 2-146 to 2-150, 2-152 to 2-162, 2-164 to 2-166, 2-169, 2-171 to2-175, 2-177 to 2-179, 2-181 to 2-202, 2-204, 2-205, 2-207 to 2-214,2-215*, 2-216 to 2-228, 2-230 to 2-235, 2-237, 2-238, 2-240 to 2-251,3-003 to 3-007, 3-010 to 3-020, 3-022 to 3-024, 3-026, 3-027, 3-029,3-030, 3-033 to 3-051, 4-013, 4-015, 5-001, 6-001, 6-003 to 6-005,7-001, 7-002, 7-004 to 7-009, 9-001 to 9-006, 10-001, 10-002, 11-001,11-002, 12-001, 12-003 to 12-006, 12-008 to 12-013, 12-015 to 12-017,13-001, 13-002, 15-001, 17-001 to 17-007, 17-009, 17-010, 18-001,19-001, 20-001 to 20-003, 20-005, 20-006, 21-001, 22-001 to 22-003,23-001 to 23-004, 24-001, 25-001, 25-002, 26-001, 26-003, 27-002 and32-028 of the present invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 3: Test on the preventive effect against cucumbergray mold (mycelium inoculation)

Cucumber (cultivar: Sagami Hanjiro) was planted in 90 cm³ plastic pots,and in the seed leaf stage, 5 ml per pot of test solutions A of thecompounds of the present invention were applied. On the next day, thepots were put in a plastic container, and agar blocks (diameter: 5 mm)containing Botrytis cinerea preliminarily cultivated in a PDA mediumwere inoculated to the seed leaves of the cucumber treated with thesolutions. After the inoculation, the plastic container was covered witha plastic sheet and humidified, and placed at 20° C. for 2 days,whereupon the proportion of the formed lesion in the inoculated leaveswas measured to calculate the control value in accordance with the sameformula as in Test Example 1. Here, the test was carried out induplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-005, 1-040, 1-041, 1-043, 1-050 to 1-052, 1-057, 1-058,1-065, 1-070, 1-072 to 1-075, 1-080, 1-083, 1-090, 1-093, 1-094, 1-099,1-100, 2-002 to 2-018, 2-020*, 2-021, 2-022, 2-024 to 2-027, 2-029,2-032, 2-040, 2-042, 2-044, 2-045, 2-047, 2-048, 2-051 to 2-054, 2-060,2-065, 2-069, 2-071, 2-074, 2-075, 2-081, 2-083, 2-085, 2-092, 2-096,2-098, 2-113, 2-114*, 2-115, 2-117, 2-118, 2-120, 2-121, 2-123, 2-124,2-126 to 2-129, 2-131 to 2-143, 2-146, 2-149, 2-152, 2-154, 2-156 to2-158, 2-160 to 2-162, 2-166 to 2-169, 2-171 to 2-174, 2-176, 2-178,2-179, 2-181 to 2-196, 2-200 to 2-202, 2-204, 2-205, 2-207 to 2-214,2-215*, 2-216 to 2-220, 2-222, 2-223, 2-225 to 2-228, 2-230 to 2-235,2-237, 2-238, 2-244 to 2-251, 3-004, 3-006, 3-007, 3-010, 3-011, 3-014,3-015, 3-018 to 3-020, 3-022, 3-023, 3-026, 3-027, 3-029, 3-033 to3-048, 3-051, 4-013, 4-015, 5-001, 6-001, 6-003, 6-005, 7-002, 7-004 to7-009, 9-001 to 9-004, 9-006, 10-001, 11-001, 11-002, 12-004, 12-008 to12-013, 12-015 to 12-017, 13-001, 13-002, 15-001, 17-002 to 17-004,17-006, 17-007, 17-010, 19-001, 20-001, 20-003, 20-005, 20-006, 21-001,22-001 to 22-003, 23-001, 24-001 and 32-028 of the present invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 4: Test on the preventive effect against cucumberstem rot

Cucumber (cultivar: Sagami Hanjiro) was planted in 90 cm³ plastic pots,and in the seed leaf stage, 5 ml per pot of test solutions A of thecompounds of the present invention were applied. After drying in air,the pots were put in a plastic container, and agar blocks (diameter: 5mm) containing Sclerotinia sclerotiorum preliminarily cultivated in aPDA medium were inoculated to the seed leaves of the cucumber treatedwith the solutions. After the inoculation, the plastic container wascovered with a plastic sheet and humidified, and placed at 20° C. for 2days, whereupon the proportion of the formed lesion in the inoculatedleaves was measured to calculate the control value in accordance withthe same formula as in Test Example 1. Here, the test was carried out induplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-001, 1-003, 1-005, 1-006, 1-036 to 1-038, 1-040, 1-041,1-043 to 1-045, 1-051, 1-053, 1-054, 1-057, 1-058, 1-060, 1-065, 1-070,1-071, 1-073 to 1-075, 1-079, 1-080, 1-092, 1-093, 1-096, 1-099, 2-002to 2-019, 2-020*, 2-021, 2-022, 2-024 to 2-030, 2-032 to 2-034, 2-040 to2-048, 2-050, 2-051, 2-053, 2-054, 2-056, 2-059, 2-060, 2-064 to 2-067,2-069, 2-071, 2-072, 2-076, 2-079, 2-081, 2-083 to 2-089, 2-091, 2-092,2-093*, 2-096 to 2-102, 2-104 to 2-111, 2-113, 2-114, 2-115, 2-117 to2-121, 2-123, 2-124, 2-126 to 2-129, 2-131 to 2-144, 2-146 to 2-169,2-171 to 2-174, 2-176 to 2-179, 2-181 to 2-205, 2-207 to 2-214, 2-215,2-216 to 2-228, 2-230 to 2-235, 2-237, 2-238, 2-240 to 2-251, 3-003,3-005 to 3-007, 3-010, 3-011, 3-014 to 3-020, 3-022 to 3-024, 3-026,3-027, 3-029, 3-030, 3-033 to 3-049, 3-051, 4-002 to 4-004, 4-013,4-015, 5-001, 6-001, 6-003 to 6-005, 7-002, 7-004 to 7-009, 9-001 to9-004, 9-006, 10-001, 10-002, 11-001, 11-002, 12-001, 12-004, 12-005,12-009 to 12-013, 12-015 to 12-017, 13-001, 13-002, 15-001, 17-002 to17-004, 17-006, 17-007, 17-009, 17-010, 19-001, 20-001 to 20-003, 20-005to 20-007, 21-001, 22-001 to 22-003, 24-001, 25-001, 26-001, 27-002 and32-028 of the present invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 5: Test on the preventive effect against wheatpowdery mildew

To wheat (cultivar: Norin-61-go) in 1.3-leaf stage planted in 90 cm³plastic pots, 5 ml per pot of test solutions A of the compounds of thepresent invention were applied. On the next day, the pots were placed inan air-conditioned greenhouse (20° C.), and conidium of Blumeriagraminis f. sp. tritici was inoculated to the wheat. 7 Days after, theproportion of the formed lesion in the inoculated leaves was measured tocalculate the control value in accordance with the same formula as inTest Example 1. Here, the test was carried out in duplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-001, 1-003, 1-005 to 1-011, 1-014, 1-040 to 1-046,1-048 to 1-060, 1-062, 1-063, 1-065 to 1-068, 1-070 to 1-075, 1-078 to1-088, 1-090 to 1-093, 1-095 to 1-102, 2-002 to 2-019, 2-020*, 2-021 to2-034, 2-036 to 2-038, 2-040 to 2-051, 2-053 to 2-075, 2-077, 2-079,2-081, 2-083 to 2-089, 2-090*, 2-091, 2-092, 2-095 to 2-111, 2-113,2-115, 2-117 to 2-121, 2-123, 2-124, 2-126 to 2-129, 2-131 to 2-134,2-136 to 2-139, 2-141 to 2-155, 2-157 to 2-192, 2-194 to 2-205, 2-207 to2-214, 2-215*, 2-216 to 2-223, 2-225 to 2-228, 2-230 to 2-235, 2-237,2-238, 2-240 to 2-251, 3-001, 3-003, 3-006, 3-007, 3-010 to 3-020, 3-022to 3-025, 3-027, 3-028, 3-030, 3-033 to 3-051, 4-002 to 4-006, 4-008 to4-011, 5-001, 6-001, 6-003, 6-005, 7-001, 7-002, 7-004 to 7-009, 9-001to 9-006, 11-002, 12-001, 12-003 to 12-006, 12-008 to 12-013, 12-015 to12-017, 13-001, 13-002, 15-001, 17-002 to 17-010, 18-001, 19-001, 20-001to 20-003, 20-005 to 20-007, 21-001, 22-001 to 22-003, 23-001, 23-002,23-004, 24-001, 25-001 to 25-004, 26-001, 26-003 and 31-007 of thepresent invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 6: Test on the preventive effective against wheatglume blotch

To wheat (cultivar: Haruyutaka) in 1.3-leaf stage planted in 90 cm³plastic pots, 5 ml per pot of test solutions A of the compounds of thepresent invention were applied. On the next day, a suspension ofconidium of Phaeosphaeria nodorum synonym: Septoria nodorum) wasspray-inoculated to the wheat, and the pots were placed in aninoculation chamber at 20° C. under a humidity of 100% for 2 days. Then,the pots were placed in an air-conditioned greenhouse (20° C.) for 6days. The proportion of the formed lesion in the inoculated leaves wasmeasured to calculate the control value in accordance with the sameformula as in Test Example 1. Here, the test was carried out induplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-041, 1-044, 1-045, 1-058, 1-067, 1-075, 1-079, 1-082 to1-084, 1-101, 1-102, 2-002 to 2-006, 2-008 to 2-010, 2-012 to 2-018,2-020*, 2-021, 2-022, 2-024 to 2-029, 2-037, 2-040 to 2-042, 2-044,2-047, 2-048, 2-063, 2-064, 2-066, 2-067, 2-071, 2-072, 2-074, 2-081,2-086, 2-087, 2-092, 2-096 to 2-099, 2-101, 2-102, 2-105, 2-012 to2-018, 2-115, 2-118, 2-120, 2-121, 2-123, 2-124, 2-127 to 2-129, 2-131,2-132, 2-134 to 2-136, 2-139, 2-141 to 2-146, 2-148, 2-158, 2-159,2-162, 2-167, 2-168, 2-171 to 2-179, 2-181, 2-183 to 2-187, 2-190 to2-196, 2-198, 2-202, 2-204, 2-205, 2-207 to 2-211, 2-214, 2-215*, 2-216,2-217, 2-219, 2-220, 2-225 to 2-227, 2-231 to 2-235, 2-237, 2-238, 2-244to 2-251, 3-007, 3-015, 3-016, 3-018, 3-020, 3-023, 3-034, 3-035, 3-038to 3-041, 3-043, 3-047, 3-050, 4-003, 5-001, 6-003, 6-005, 7-007 to7-009, 9-002, 9-003, 10-001, 12-008, 12-009, 12-011, 12-013, 12-015,13-001, 15-001, 17-004, 17-009, 20-001 to 20-003, 20-006, 22-001, 22-003and 25-001 to 25-004 of the present invention.

The symbol * means that the test was carried out using a 100 ppmsolution. TEST EXAMPLE 7: Test on the preventive effect against wheatbrown leaf rust

To wheat (cultivar: Norin-61-go) in 1.3-leaf stage planted in 90 cm³plastic pots, 5 ml per pot of test solutions A of the compounds of thepresent invention were applied. On the next day, a suspension of sporeof Puccinia recondita was spray-inoculated to the wheat, and the potswere placed in an inoculation chamber at 20° C. under a humidity of 100%for 1 day. Then, the pots were placed in an air-conditioned greenhouse(20° C.) for 8 days. The proportion of the formed lesion in theinoculated leaves was measured to calculate the control value inaccordance with the same formula as in Test Example 1. Here, the testwas carried out in duplicate.

As a result, among the compounds tested, the following compounds showeda control value of at least 70%.

Compounds Nos. 1-013, 1-046, 1-049, 1-053, 1-054, 1-057, 1-065 to 1-068,1-071, 1-075, 1-079, 1-084 to 1-086, 1-090 to 1-092, 1-095, 2-005,2-033, 2-075, 2-102, 2-106 to 2-110, 2-115, 2-117, 2-118, 2-120, 2-121,2-123, 2-124, 2-126, 2-127, 2-129, 2-131 to 2-133, 2-136, 2-137, 2-141,2-142, 2-158, 2-172, 2-174, 2-178, 2-179, 2-184, 2-186 to 2-188, 2-207to 2-210, 2-214, 2-226, 2-232, 2-234, 2-237, 2-238, 2-248, 2-249, 3-016to 3-018, 3-038, 3-039, 3-043, 3-044, 4-004, 5-001, 6-003, 7-004, 9-002,12-009, 12-013, 12-016, 13-001, 17-010, 22-003, 25-001, 26-003, 30-011,31-007 and 32-012 of the present invention.

Test Example 8

Test on the Antibacterial Activity on Aspergillus niger

60 μl of a potato dextrose 1% agar medium was added to each well of a 96well plate, and 30 μl of sterilized water containing spores ofAspergillus niger (10 spores/3 μl) was added to each well. Further, 10μl per well of test solutions B of the compounds of the presentinvention were added, and the plate was left at rest at 25° C. underdark conditions. 2 Days after addition of the solutions, the flora arearatio (%) was determined to calculate the efficacy (%) relative to thenon-treated plot in accordance with the following formula.

Efficacy(%)=[1−(flora area ratio in treated plot/flora area ratio innon-treated plot)]×100

As a result, among the compounds tested, the following compounds showedan efficacy of at least 50%.

Compounds Nos. 1-001, 1-003, 1-005 to 1-008, 1-020, 1-036 to 1-038,1-040, 1-041, 1-043 to 1-054, 1-056 to 1-070, 1-072 to 1-074, 1-080,1-081, 1-083 to 1-087, 1-089, 1-090, 1-092 to 1-094, 1-096, 1-097, 1-099to 1-102, 2-002 to 2-005, 2-007 to 2-019, 2-021, 2-024, 2-026 to 2-030,2-032 to 2-034, 2-037, 2-040 to 2-042, 2-044 to 2-051, 2-053, 2-054,2-056 to 2-061, 2-064 to 2-076, 2-079 to 2-081, 2-084, 2-086 to 2-089,2-091 to 2-111, 2-114, 2-115, 2-117 to 2-124, 2-126 to 2-129, 2-132 to2-137, 2-139 to 2-152, 2-154, 2-156 to 2-164, 2-166 to 2-169, 2-171 to2-176, 2-181 to 2-197, 2-199 to 2-205, 2-207 to 2-212, 2-216 to 2-221,2-223 to 2-227, 2-230 to 2-238, 2-245, 2-246, 3-003, 3-006, 3-007, 3-010to 3-025, 3-029, 3-030, 3-036, 3-040, 4-002, 4-003, 7-001, 7-002, 7-004,7-005, 7-007, 7-009, 9-001, 9-002, 9-004, 10-002, 12-001, 12-005,12-006, 12-008, 12-010, 12-011, 13-001, 15-001, 17-001 to 17-010,19-001, 20-001 to 20-003, 21-001, 22-001 to 22-003, 23-001 to 23-004,26-001, 26-003 and 28-001 of the present invention.

Test Example 9 Insecticidal Test on Meloidogyne incognita

60 μl of a potato dextrose 1% agar medium was added to each well of a 96well plate, and 30 μl of sterilized water containing eggs of Meloidogyneincognita (10 eggs/3 μl) was added to each well. Further, 10 μl per wellof test solutions B of the compounds of the present invention wereadded, and the plate was left at rest at 25° C. under dark conditions. 4Days after addition of the solutions, unhatched eggs and inactive larvaewere counted, to calculate the efficacy (%) relative to the non-treatedplot in accordance with the following formula.

Efficacy(%)=[(number of unhatched eggs+inactive larvae in treatedplot)/number of active larvae in non-treated plot]×100

As a result, among the compounds tested, the following compounds showedan efficacy of at least 50%.

Compounds Nos. 1-001, 1-003, 1-005 to 1-007, 1-009, 1-020, 1-021, 1-023,1-025, 1-040, 1-043, 1-047 to 1-053, 1-058 to 1-061, 1-063 to 1-069,1-072, 1-078, 1-081, 1-083, 1-092 to 1-096, 1-099 to 1-102, 2-002 to2-019, 2-022, 2-024, 2-027 to 2-030, 2-032, 2-033, 2-036 to 2-040,2-042, 2-044 to 2-048, 2-050, 2-051, 2-053 to 2-061, 2-064 to 2-067,2-069, 2-071 to 2-075, 2-079 to 2-081, 2-083 to 2-085, 2-087, 2-088,2-091 to 2-094, 2-096 to 2-111, 2-114, 2-115, 2-117 to 2-124, 2-126 to2-133, 2-135 to 2-142, 2-146, 2-150 to 2-152, 2-157 to 2-164, 2-166 to2-174, 2-176, 2-178, 2-180 to 2-189, 2-192, 2-194 to 2-197, 2-199 to2-202, 2-204, 2-205, 2-207 to 2-210, 2-212, 2-216, 2-217, 2-220, 2-221,2-223, 2-226, 2-227, 2-230 to 2-238, 2-245, 2-246, 2-248, 2-249, 2-251,3-001, 3-002, 3-004 to 3-008, 3-010, 3-011, 3-014 to 3-025, 3-029,3-030, 3-036, 3-040, 3-045, 3-049, 3-051, 4-002, 4-003, 7-002, 7-004,7-005, 7-007, 7-009, 9-001 to 9-004, 12-001, 12-002, 12-005, 12-008,12-010, 12-011, 12-013, 12-017, 13-001, 17-002, 23-001, 26-001 and26-003 of the present invention.

Test Example 10 Test on the Preventive Effect on Meloidogyne Incognita

1 ml per seedling of test solutions B of the compounds of the presentinvention were treated to the bases of garden balsam seedlings (about 2weeks after budding) planted in a cell tray of which each cell wasfilled with 10 g of soil. 1 Hour after the application, 1 ml per cell ofwater containing Meloidogyne incognita 2 L larvae (100 2 L larvae/1 ml)was applied to the bases. The tray was placed in a greenhouse for 3weeks, and the root knot level formed on the root was determined inaccordance with the following damage index and the damage degree tocalculate the efficacy (%) relative to the non-treated plot inaccordance with the following formula.

<Damage Index>

0: No knot observed.1: Knot observed on a part of the root system.2: Knot observed on the entire root system.3: Large knot observed.4: Large knot observed on the entire root system.

[Damage degree]=[Σ(damage index×number of seedlings at eachindex)/(4×number of seedlings investigated)]×100

Efficacy(%)=[1−(damage degree in treated plot/damage degree innon-treated plot)]×100

As a result, among the compounds tested, the following compounds showedan efficacy of at least 50%.

Compounds Nos. 1-006, 1-061, 1-063, 1-099, 2-002 to 2-006, 2-008, 2-009,2-011 to 2-013, 2-022, 2-024, 2-030, 2-032, 2-033, 2-044, 2-048, 2-051,2-057, 2-058, 2-060, 2-061, 2-064, 2-066, 2-067, 2-069, 2-071 to 2-074,2-079, 2-087, 2-088, 2-097 to 2-100, 2-102 to 2-105, 2-114, 2-115,2-117, 2-120, 2-121, 2-126, 2-128, 2-129, 2-133, 2-135, 2-141, 2-142,2-150, 2-151, 2-160 to 2-163, 2-166 to 2-171, 2-173, 2-174, 2-176,2-178, 2-181, 2-182, 2-196, 2-199, 2-201, 2-202, 2-205, 2-209, 2-212,2-216, 2-217, 2-237, 3-006, 3-010, 3-014, 3-016 to 3-018, 3-020, 3-021,3-029, 3-030, 7-002, 7-005 and 12-010 of the present invention.

Test Example 11 Insecticidal Test on Pratylenchus Coffeae

60 μl of a potato dextrose 1% agar medium was added to each well of a 96well plate, and 30 μl of sterilized water containing Pratylenchuscoffeae 2 L larvae cultured in callus was added to each well. Further,10 μl per well of test solutions B of the compounds of the presentinvention were added, and the plate was left at rest at 25° C. underdark conditions. 4 Days after addition of the solutions, inactive larvaewere counted to calculate the efficacy (%) relative to the non-treatedplot in accordance with the following formula.

Efficacy(%)=(number of inactive larvae in treated plot/number of activelarvae in non-treated plot)×100

As a result, among the compounds tested, the following compounds showedan efficacy of at least 50%.

Compounds Nos. 1-001, 1-003, 1-005 to 1-007, 1-058 to 1-061, 1-063,1-064, 1-099, 2-002 to 2-018, 2-022, 2-024, 2-027, 2-029, 2-030, 2-032to 2-034, 2-036 to 2-040, 2-042, 2-044, 2-046 to 2-048, 2-050, 2-051,2-053 to 2-058, 2-060, 2-061, 2-064 to 2-067, 2-069, 2-071 to 2-075,2-079 to 2-081, 2-083 to 2-085, 2-087, 2-088, 2-091, 2-093, 2-094, 2-096to 2-108, 2-110, 2-115, 2-117, 2-120, 2-121, 2-129, 2-139, 2-141, 2-146,2-150, 2-159 to 2-164, 2-166 to 2-171, 2-173, 2-176, 2-178, 2-181,2-197, 2-199 to 2-202, 3-002, 3-005, 3-006, 3-008, 3-010, 3-014, 3-016to 3-018, 3-020 to 3-023, 3-025, 3-030, 3-031, 7-002, 7-005, 12-002,12-005, 12-008, 12-010 and 17-002 of the present invention.

Test Example 12 Insecticidal Test on Haemonchus contortus

60 μl of a potato dextrose 1% agar medium was added to each plate of a96 well plate, and 30 μl of sterilized water containing eggs ofHaemonchus contortus (10 eggs/3 μl) was added to each well. Further, 10μl per well of test solutions B of the compounds of the presentinvention were added, and the plate was left at rest at 25° C. underdark conditions. 4 Days after addition of the solutions, unhatched eggsand inactive larvae were counted to calculate the efficacy (%) relativeto the non-treated plot in accordance with the same formula as in TestExample 9.

As a result, among the compounds tested, the following compounds showedan efficacy of at least 50%.

Compounds Nos. 1-001 to 1-013, 1-017 to 1-021, 1-023, 1-024, 1-026,1-028, 1-029, 1-031, 1-032, 1-034, 1-036 to 1-074, 1-080, 1-081, 1-083to 1-094, 1-096, 1-097, 1-099 to 1-102, 2-001 to 2-019, 2-021 to 2-027,2-029, 2-030, 2-032 to 2-051, 2-053 to 2-061, 2-064 to 2-089, 2-091 to2-115, 2-117 to 2-129, 2-132 to 2-137, 2-139 to 2-164, 2-166 to 2-178,2-180 to 2-197, 2-199 to 2-212, 2-216 to 2-221, 2-223 to 2-227, 2-230 to2-238, 2-245, 2-246, 3-001 to 3-008, 3-010, 3-011, 3-013 to 3-030,3-036, 3-040, 3-049, 4-002, 4-003, 7-001, 7-002, 7-004, 7-005, 7-007,7-009, 8-001, 9-002, 9-004, 10-002, 12-001 to 12-008, 12-010, 12-011,13-001, 15-001, 17-001, 17-003, 17-004, 17-006, 20-002, 20-003, 22-001,22-002, 23-001 to 23-004, 26-001 to 26-003, 29-001 and 29-002 of thepresent invention.

INDUSTRIAL APPLICABILITY

The oxime-substituted amide compounds of the present invention are veryuseful compounds which are excellent in pesticidal activities,especially in fungicidal and nematocidal activities, and have littleharmful effect on non-target organisms such as mammals, fishes anduseful insects.

The entire disclosures of Japanese Patent Application No. 2012-156398filed on Jul. 12, 2012, Japanese Patent Application No. 2013-019666filed on Feb. 4, 2013 and Japanese Patent Application No. 2013-103989filed on May 16, 2013 including specifications, claims and summaries areincorporated herein by reference in their entireties.

1. An oxime-substituted amide compound represented by formula (I), orits N-oxide or salt:

wherein: G¹ is a structure represented by any one of G¹-1 to G¹-51:

G² is a structure represented by any one of G²-1 to G²-19:

W is an oxygen atom or a sulfur atom; X¹ is a halogen atom, cyano,nitro, —SF₅, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R⁶,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, —OR⁷, —S(O)_(r)R⁷,—N(R⁹)R⁸, —C(O)NH₂, —C(S)NH₂, tri(C₁-C₆ alkyl)silyl, phenyl, phenylsubstituted with (Z)_(m) or D-3; each of X², X³, X⁴ and X⁵ isindependently a hydrogen atom, a halogen atom, cyano, nitro, C₁-C₆alkyl, (C₁-C₆)alkyl optionally substituted with R⁶, C₃-C₈ cycloalkyl,C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,C₂-C₆ haloalkynyl, —OH, —OR⁷, —SH, —S(O)_(r)R⁷, —N(R⁹)R⁸, C₁-C₆alkylcarbonyl, C₁-C₆ alkoxycarbonyl, —C(O)NH₂, —C(S)NH₂, phenyl, phenylsubstituted with (Z)_(m), D-2 or D-32, provided that when G₁ is astructure represented by G¹-27 and X¹ is dihalomethyl, X² is a hydrogenatom; each of Y¹ and Y³ is independently a hydrogen atom, a halogenatom, cyano, nitro, —SCN, —SF₅, C₁-C₈ alkyl, (C₁-C₆)alkyl optionallysubstituted with R⁶, C₃-C₁₀ cycloalkyl, (C₃-C₁₀)cycloalkyl optionallysubstituted with R⁶, E-1 to E-22, C₂-C₆ alkenyl, (C₂-C₆)alkenyloptionally substituted with R⁶, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, C₂-C₆ alkynyl, (C₂-C₆)alkynyl optionally substitutedwith R⁶, —OH, —OR⁷, —OS(O)₂R⁷, —SH, —S(O)_(r)R⁷, —N(R⁹)R⁸,—N═C(R^(9a))R^(8a), —C(O)R¹⁰, —C(R¹⁰)═NOH, —C(R¹⁰)═NOR¹¹, M-3, M-13,M-30, —C(O)OH, —C(O)OR¹¹, —C(O)SR¹¹, —C(O)N(R¹³)R¹², M-7, M-17, M-23,M-26, —C(S)OR¹¹, —C(S)SR¹¹, —C(S)N(R¹³)R¹², M-9, M-19, M-23, M-24, M-28,M-25, M-29, —S(O)₂OR¹¹, —S(O)₂N(R¹³)R¹², —Si(R^(14a))(R^(14b))R¹⁴,phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38; each of Y², Y⁴and Y⁵ is independently a hydrogen atom, a halogen atom, cyano, nitro,—SCN, —SF₅, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R⁶,C₃-C₈ cycloalkyl, C₃-C₃ halocycloalkyl, —OH, —OR⁷, —SH, —S(O)_(r)R⁷,—NH₂, C₁-C₆ alkylamino, di(C₁-C₆ alkyl)amino, C₂-C₆ alkenyl, C₂-C₆haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₁-C₆ alkoxycarbonyl,—C(O)NH₂ or —C(S)NH₂, or, Y¹, Y², Y³ and Y⁴ represent that Y¹ or Y³ andY², or Y³ and Y⁴, together form —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—,—OCH₂O—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂N(R⁵)—,—CH₂N(R⁵)CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—,—OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —CH₂CH═CH—, —N(R⁵)N═CH—,—OCH₂CH═CH—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═N— or—N═CHCH═N— to form a 5-membered ring or a 6-membered ring together withthe carbon atoms attached to Y¹, Y², Y³ and Y⁴, wherein hydrogen atomson the respective ring-constituting carbon atoms are optionallysubstituted with a halogen atom, cyano, nitro, C₁-C₄ alkyl or C₁-C₄haloalkyl, and further, when G¹ is a structure represented by G¹-1,G¹-9, G¹-10, G¹-12, G¹-13, G¹-16 to G¹-20, G¹-22 to G¹-24, G¹-26, G¹-27,G¹-30, G¹-32, G¹-35, G¹-38, G¹-40 or G¹-42 to G¹-50, Y¹ and Y², Y² andY³, or Y³ and Y⁴, together optionally form —OCH═CH—, —SCH═CH—,—N(R⁵)CH═CH—, —OCH═N—, —SCH═N— or —N(R⁵)CH═N— to form a 5-membered ringtogether with the carbon atoms attached to Y¹, Y², Y³ and Y⁴, whereinhydrogen atoms on the respective ring-constituting carbon atoms areoptionally substituted with a halogen atom, cyano, nitro, C₁-C₄ alkyl orC₁-C₄ haloalkyl; D-1 to D-38 are aromatic heterocyclic rings representedby the following structural formulae, respectively:

E-1 to E-22 are saturated heterocyclic rings represented by thefollowing structural formulae, respectively:

Z is a halogen atom, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, haloalkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl,C₁-C₄ haloalkylthio(C₁-C₄)alkyl, alkylsulfinyl(C₁-C₄)alkyl,haloalkylsulfinyl(C₁-C₄)alkyl, C₁-C₄ alkylsulfonyl(C₁-C₄)alkyl, C₁-C₄haloalkylsulfonyl(C₁-C₄)alkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl,—OH, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylsulfonyloxy, C₁-C₄haloalkylsulfonyloxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylsulfonyl, —NH₂, C₁-C₄ alkylamino, di(C₁-C₄ alkyl)amino, C₁-C₄alkoxycarbonyl, C₁-C₄ haloalkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl, di(C₁-C₄ alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂ orphenyl; when m or n is an integer of at least 2, the respective Z's areidentical with or different from one another, and when there are twoneighboring Z's, the two neighboring Z's optionally form —CH₂CH₂CH₂—,—CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—,—CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—,—OCH₂CH₂S— or —CH═CH—CH═CH— to form a 5-membered ring or a 6-memberedring together with the carbon atoms attached to the two Z's, whereinhydrogen atoms on the respective ring-constituting carbon atoms areoptionally substituted with a halogen atom, a cyano group, a nitrogroup, a methyl group, a trifluoromethyl group, a methoxy group or amethylthio group; R¹ is C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substitutedwith R¹⁸, C₃-C₁₀ cycloalkyl, C₃-C₁₀ halocycloalkyl, E-2 to E-8, E-14 toE-18, E-21, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₅-C₁₀ cycloalkenyl,C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl,phenyl(C₃-C₆)alkynyl, phenyl or phenyl substituted with (Z)_(m); R² is ahydrogen atom, cyano, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄alkylsulfinyl(C₁-C₄)alkyl, C₁-C₄ alkylsulfonyl-(C₁-C₄)alkyl, C₃-C₆cycloalkyl or phenyl, or optionally forms a ring together with R³,provided that when G¹ is a structure represented by G¹-1, X¹ is achlorine atom, X², X³ and X⁵ are hydrogen atoms, X⁴ is a hydrogen atomor a chlorine atom, G² is a structure represented by G²-1, Y³ is achlorine atom, and Y¹, Y², Y⁴ and Y⁵ are hydrogen atoms, R² is cyano,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, C₁-C₄ alkylsulfinyl(C₁-C₄)alkyl,alkylsulfonyl(C₁-C₄)alkyl, C₃-C₆ cycloalkyl or phenyl; R³ is a hydrogenatom or C₁-C₆ alkyl, or R³ optionally forms, together with R², a C₂-C₅alkylene chain to form a 3- to 6-membered ring together with the carbonatom attached to R² and R³, wherein the alkylene chain optionallycomprises an oxygen atom, sulfur atom or nitrogen atom, and isoptionally substituted with a C₁-C₄ alkyl group, a —CHO group, a C₁-C₄alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group, a C₁-C₄alkylaminocarbonyl group, a C₁-C₄ haloalkylaminocarbonyl group, adi(C₁-C₄ alkyl)aminocarbonyl group or a phenyl group; R⁴ is a hydrogenatom, cyano, nitro, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R¹⁹, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₅-C₁₀cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl,—C(O)R²⁰, —C(O)OR²¹, —C(O)SR²¹, —C(O)N(R²³)R²², —C(O)C(O)OR²¹,—C(S)OR²¹, —C(S)SR²¹, —C(S)N(R²³)R²², —OH, —OR²¹, —SR²¹, —N(R²⁵)R²⁴,—N═C(R^(25a))R^(24a), —S(O)₂R²¹, —S(O)₂N(R²³)R²² or —SN(R²⁷)R²⁶; R⁵ is ahydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl(C₁-C₄)alkyl, C₃-C₆ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynylor C₂-C₆ haloalkynyl; R⁶ is a halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, hydroxy(C₃-C₃)cycloalkyl, C₁-C₆alkoxy(C₃-C₈)cycloalkyl, C₃-C₆ alkenyl, C₃-C₈ cycloalkenyl, E-1 to E-22,—OH, —OR⁷, —SH, —S(O)_(n)R⁷, —N(R⁹)R⁸,)-C(R¹⁰)═NOH, —C(R¹⁰)═NOR¹¹,—C(O)OR¹¹, —C(O)N(R¹³)R¹², —Si(R^(14a))(R^(14b))R¹⁴, phenyl, phenylsubstituted with (Z)_(m) or D-1 to D-38; R⁷ is C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈ cycloalkyl,(C₃-C₈)cycloalkyl optionally substituted with R²⁸, E-2 to E-8, E-14 toE-18, E-21, C₂-C₆ alkenyl, (C₂-C₆)alkenyl optionally substituted withR²⁸, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl,(C₃-C₆)alkynyl optionally substituted with R²⁸, C₁-C₆ alkylcarbonyl,C₁-C₆ alkoxycarbonyl, phenyl, phenyl substituted with (Z)_(m), D-1, D-2,D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 toD-38; R⁸ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionallysubstituted with R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₆alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, —C(O)R¹⁰,—C(O)C(O)R¹¹, —C(O)OR¹¹, —C(O)C(O)OR¹¹, —C(O)SR¹¹, —C(O)N(R¹³)R¹²,—C(S)OR¹¹, —C(S)SR¹¹, —C(S)N(R¹³)R¹², —OH, —S(O)₂R¹¹ or —S(O)₂N(R¹³)R¹²,or optionally forms a ring together with R⁹; R⁹ is a hydrogen atom,C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, —CHO, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl or C₁-C₆alkoxycarbonyl, or R⁹ optionally forms, together with R⁸, a C₂-C₆alkylene chain to form a 3- to 7-membered ring together with thenitrogen atom attached to R⁸ and R⁹, wherein the alkylene chainoptionally comprises an oxygen atom, sulfur atom or nitrogen atom, andis optionally substituted with a halogen atom, a C₁-C₄ alkyl group, aC₁-C₄ haloalkyl group, an oxo group or a thioxo group; R^(8a) is C₁-C₆alkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ alkenyloxy, phenoxy orphenoxy substituted with (Z)_(m), or optionally forms a ring togetherwith R^(9a); R^(9a) is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₆ alkenyl, phenyl or phenyl substituted with (Z)_(m), or R^(9a)optionally forms, together with R^(8a), a C₄-C₆ alkylene chain to form a5- to 7-membered ring together with the carbon atom attached to R^(8a)and R^(9a), wherein the alkylene chain optionally comprises an oxygenatom or sulfur atom; R¹⁰ is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyloptionally substituted with R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, phenyl, phenylsubstituted with (Z)_(m), or D-1 to D-38; R¹¹ is C₁-C₆ alkyl,(C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₅-C₁₀ cycloalkenyl,C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, phenyl,phenyl substituted with (Z)_(m), D-1, D-2, D-4 to D-6, D-8 to D-10, D-12to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38; R¹² is a hydrogen atom,C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl,C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, phenylcarbonyl, C₁-C₆ alkoxycarbonyl, phenyl, phenylsubstituted with (Z)_(m), D-1 to D-25 or D-27 to D-38, or optionallyforms a ring together with R¹³; R¹³ is a hydrogen atom, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl(C₁-C₄) alkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄alkylsulfonyl(C₁-C₄) alkyl, cyano(C₁-C₄)alkyl, C₃-C₆ alkenyl or C₃-C₆alkynyl, or R¹³ optionally forms, together with R¹², a C₂-C₆ alkylenechain to form a 3- to 7-membered ring together with the nitrogen atomattached to R¹² and R¹³, wherein the alkylene chain optionally comprisesan oxygen atom, sulfur atom or nitrogen atom, and is optionallysubstituted with a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ alkoxygroup, a —CHO group, a C₁-C₄ alkylcarbonyl group or a C₁-C₄alkoxycarbonyl group; R¹⁴ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy,phenyl or phenyl substituted with (Z)_(m); each of R^(14a) and R^(14b)is independently C₁-C₆ alkyl, C₁-C₆ haloalkyl or C₁-C₆ alkoxy; R¹⁵ is ahydrogen atom, cyano, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl(C₁-C₄)alkyl, hydroxy(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl,C₁-C₄ haloalkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄haloalkylthio(C₁-C₄)alkyl, C₁-C₄ alkylamino(C₁-C₄)alkyl, di(C₁-C₄alkyl)amino(C₁-C₄)alkyl, cyano(C₁-C₄)alkyl, C₁-C₄alkoxycarbonyl(C₁-C₄)alkyl, C₁-C₄ haloalkoxycarbonyl(C₁-C₄)alkyl,phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₆cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆haloalkynyl, C₁-C₆ alkylcarbonyl, phenylcarbonyl, phenylcarbonylsubstituted with (Z)_(m), C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, di(C₁-C₆ alkyl)aminocarbonyl, C₁-C₆ alkylsulfonyl,phenylsulfonyl, phenylsulfonyl substituted with (Z)_(m), di(C₁-C₆alkyl)aminosulfonyl, phenyl, phenyl substituted with (Z)_(m), or C₁-C₆alkoxy, and further, when R¹⁵ and Z are neighboring, the neighboring R¹⁵and Z optionally form —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—,—CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N— to form a 6-membered ringtogether with the atoms respectively attached to R¹⁵ and Z, whereinhydrogen atoms on the respective ring-constituting carbon atoms areoptionally substituted with a halogen atom, a methyl group or atrifluoromethyl group; R¹⁶ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, —C(O)R¹⁰, —C(O)C(O)R¹¹,—C(O)OR¹¹, —C(O)C(O)OR¹¹, —C(O)SR¹¹, —C(O)N(R¹³)R¹², —C(S)OR¹¹,—C(S)SR¹¹, —C(S)N(R¹³)R¹², —S(O)₂R¹¹, —S(O)₂N(R¹³)R¹², phenyl, phenylsubstituted with (Z)_(m) or D-3; R^(16a) is a hydrogen atom, cyano,nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆ haloalkylsulfonyl; R¹⁷ is a halogen atom, cyano,C₁-C₆ alkyl, C₁-C₆ haloalkyl, hydroxy(C₁-C₄)alkyl, C₁-C₄alkoxy(C₁-C₄)alkyl, C₁-C₄ alkoxycarbonyl(C₁-C₄)alkyl, C₁-C₆ alkoxy,C₁-C₆ alkylthio, C₁-C₆ alkylamino, di(C₁-C₆ alkyl)amino, C₁-C₆alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(m), such thatwhen p is an integer of at least 2, the respective R¹⁷'s are optionallyidentical with or different from one another, and further, when twoR¹⁷'s are on the same carbon atom, the two R¹⁷'s together optionallyform C₁-C₄ alkylidene, oxo, thioxo, imino, C₁-C₄ alkylimino or C₁-C₄alkoxyimino; R¹⁸ is a halogen atom, cyano, nitro, C₃-C₁₀ cycloalkyl,C₃-C₁₀ halocycloalkyl, E-1 to E-22, C₅-C₁₀ cycloalkenyl, C₅-C₁₀halocycloalkenyl, —OR²⁹, —N(R³⁰)R²⁹, —SH, —S(O)_(r)R³¹,—S(O)_(t)(R³¹)═NR^(16a), —C(O)R³², —C(R³²)═NOH, —C(R³²)═NOR³³, —C(O)OH,—C(O)OR³³, —C(O)SR³³, —C(O)N(R³⁵)R³⁴, —C(O)C(O)OR³³, —C(S)OR³³,—C(S)SR³³, —C(S)N(R³⁵)R³⁴, —S(O)₂OH, —S(O)₂OR³³, —S(O)₂N(R³⁵)R³⁴,—Si(R^(14a))(R^(14b))R¹⁴, M-1 to M-30, phenyl, phenyl substituted with(Z)_(m) or D-1 to D-38; M-1 to M-30 are partial saturated heterocyclicrings represented by the following structural formulae, respectively:

R¹⁹ is a halogen atom, cyano, nitro, C₃-C₈ cycloalkyl, E-5, E-6, E-14,E-15, C₅-C₁₀ cycloalkenyl, —OR³⁶, —S(O)_(n)R³⁷, —C(R³²)═NOH,—C(R³²)═NOR³³, M-3, —C(O)OR³³, —C(O)SR³³, —C(O)NH₂, M-7, M-17,—C(O)C(O)OR³³, —C(S)OR³³, —C(S)SR³³, —C(S)NH₂, M-9, M-19,—S(O)₂N(R³⁵)R³⁴ or —Si(R^(14a))(R^(14b))R¹⁴; R²⁰ is a hydrogen atom,C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R²⁸, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl,C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₂-C₆ alkynyl or C₂-C₆haloalkynyl; R²¹ is C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₅-C₁₀ cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₃-C₆ alkynylor C₃-C₆ haloalkynyl; R²² is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyloptionally substituted with R²⁸, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl,C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, phenylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl, phenyl substituted with (Z)_(m), D-1 to D-25 orD-27 to D-38, or optionally forms a ring together with R²³; R²³ is ahydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl(C₁-C₄)alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄ alkylthio(C₁-C₄)alkyl, C₁-C₄alkylsulfonyl(C₁-C₄) alkyl, cyano(C₁-C₄)alkyl, C₃-C₆ alkenyl or C₃-C₆alkynyl, or R²³ optionally forms, together with R²², a C₂-C₆ alkylenechain to form a 3- to 7-membered ring together with the nitrogen atomattached to R²² and R²³, wherein the alkylene chain optionally comprisesan oxygen atom, sulfur atom or nitrogen atom, and is optionallysubstituted with a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ alkoxygroup, a —CHO group, a C₁-C₄ alkylcarbonyl group or a C₁-C₄alkoxycarbonyl group; R²⁴ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₃-C₈ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, —S(O)₂R³³ or—S(O)₂N(R³⁵)R³⁴, or optionally forms a ring together with R^(25a); R²⁵is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl or C₃-C₆ haloalkynyl, or R²⁵ optionallyforms, together with R²⁴, a C₄-C₅ alkylene chain to form a 5- to6-membered ring together with the nitrogen atom attached to R²⁴ and R²⁵,wherein the alkylene chain optionally comprises an oxygen atom, sulfuratom or nitrogen atom, and is optionally substituted with a halogenatom, a C₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a C₁-C₄ alkoxygroup, a —CHO group, a C₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonylgroup, an oxo group or a thioxo group; R^(24a) is a hydrogen atom, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, phenyl or phenyl substitutedwith (Z)_(m), or optionally forms a ring together with R^(25a), R^(25a)is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio ordi(C₁-C₆ alkyl)amino, or R^(25a) optionally forms, together withR^(24a), a C₃-C₅ alkylene chain to form a 4- to 6-membered ring togetherwith the carbon atom attached to R^(24a) and R^(25a), wherein thealkylene chain optionally comprises an oxygen atom, sulfur atom ornitrogen atom, and is optionally substituted with a halogen atom, aC₁-C₄ alkyl group, a C₁-C₄ haloalkyl group, a —CHO group, a C₁-C₄alkylcarbonyl group or a C₁-C₄ alkoxycarbonyl group; R²⁶ is C₁-C₁₂alkyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ alkoxy(C₁-C₁₂)alkyl, cyano(C₁-C₁₂)alkyl, C₁-C₁₂ alkoxycarbonyl(C₁-C₁₂)alkyl, phenyl(C₁-C₄)alkyl,phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₁₂ alkenyl, C₃-C₁₂haloalkenyl, C₃-C₁₂ alkynyl, C₃-C₁₂ haloalkynyl, C₁-C₁₂ alkylcarbonyl,C₁-C₁₂ alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃, —C(O)ON═C(SCH₃)C(O)N(CH₃)₂,phenyl or phenyl substituted with (Z)_(m), or optionally forms a ringtogether with R²⁷; R²⁷ is C₁-C₁₂ alkyl, C₁-C₁₂ haloalkyl, C₁-C₁₂alkoxy(C₁-C₁₂ alkyl), cyano(C₁-C₁₂) alkyl, C₁-C₁₂alkoxycarbonyl(C₁-C₁₂)alkyl, phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkylsubstituted with (Z)_(m), C₃-C₁₂ alkenyl, C₃-C₁₂ haloalkenyl, C₃-C₁₂alkynyl, C₃-C₁₂ haloalkynyl, phenyl or phenyl substituted with (Z)_(m),or R²⁷ optionally forms, together with R²⁶, a C₄-C₇ alkylene chain toform a 5- to 8-membered ring together with the nitrogen atom attached toR²⁶ and R²⁷, wherein the alkylene chain optionally comprises an oxygenatom or sulfur atom, and is optionally substituted with a C₁-C₄ alkylgroup or a C₁-C₄ alkoxy group; R²⁸ is a halogen atom, cyano, nitro,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkylamino, di(C₁-C₆ alkyl)amino, C₁-C₆ alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, —C(O)NH₂, C₁-C₆ alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl, —C(S)NH₂, phenyl, phenyl substituted with (Z)_(m),or D-1 to D-38; R²⁹ is a hydrogen atom, C₁-C₈ alkyl, (C₁-C₈)alkyloptionally substituted with R³⁸, C₃-C₈ cycloalkyl, (C₃-C₈)cycloalkyloptionally substituted with R³⁸, E-2 to E-6, E-8, E-14 to E-21, C₃-C₈alkenyl, (C₃-C₈)alkenyl optionally substituted with R³⁸, C₃-C₈ alkynyl,(C₃-C₈) alkynyl optionally substituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰,—C(O)OR⁴⁰, —C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹,—C(S)OR⁴⁰, —C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹, —S(O)₂R⁴⁰, —S(O)₂N(R⁴²)R⁴¹,—Si(R^(14a))(R^(14b))R¹⁴, —P(O)(OR⁴³)₂, —P(S)(OR⁴³)₂, phenyl, phenylsubstituted with (Z)_(m), D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 toD-19, D-21, D-23, D-25, D-27 or D-30 to D-38, or optionally forms a ringtogether with R³⁰; R³⁰ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₃-C₄ cycloalkyl(C₁-C₄) alkyl, C₁-C₄ alkoxy(C₁-C₄)alkyl, C₁-C₄alkylthio(C₁-C₄)alkyl, cyano(C₁-C₄)alkyl, C₃-C₆ cycloalkyl, C₃-C₆alkenyl, C₃-C₆ alkynyl, C₁-C₆ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkoxy, C₁-C₆ alkylsulfonyl, phenyl or phenyl substituted with(Z)_(m), or R³⁰ optionally forms, together with R²⁹, a C₂-C₆ alkylenechain to form a 3- to 7-membered ring together with the nitrogen atomattached to R²⁹ and R³⁰, wherein the alkylene chain optionally comprisesan oxygen atom, sulfur atom or nitrogen atom, and is optionallysubstituted with a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ haloalkylgroup, a C₁-C₄ alkoxy group, a —CHO group, a C₁-C₄ alkylcarbonyl group,a C₁-C₄ alkoxycarbonyl group, a phenyl group, a phenyl group substitutedwith (Z)_(m), an oxo group or a thioxo group; R³¹ is C₁-C₈ alkyl,(C₁-C₈)alkyl optionally substituted with R³⁸, C₃-C₈ cycloalkyl,(C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 to E-6, E-8, E-14to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyl optionally substituted with R³⁸,C₃-C₈ alkynyl, (C₃-C₈)alkynyl optionally substituted with R³⁸, —C(O)R³⁹,—C(O)C(O)R⁴⁰, —C(O)OR⁴⁰, —C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹,—C(S)R³⁹, —C(S)OR⁴⁰, —C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹, —SH, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, phenylthio, phenylthio substituted with (Z)_(m),—P(O)(OR⁴³)₂, —P(S)(OR⁴³)₂, phenyl, phenyl substituted with (Z)_(m),D-9, D-10, D-12, D-14 to D-17, D-30 or D-32 to D-35; R³² is a hydrogenatom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl(C₁-C₄) alkyl, C₁-C₆alkoxy(C₁-C₄)alkyl, C₁-C₆ haloalkoxy(C₁-C₄)alkyl, C₁-C₆alkylthio(C₁-C₄)alkyl, C₁-C₆ haloalkylthio(C₁-C₄)alkyl, C₁-C₆alkylsulfonyl(C₁-C₄)alkyl, C₁-C₆ haloalkylsulfonyl (C₁-C₄)alkyl,phenyl(C₁-C₄)alkyl, phenyl(C₁-C₄)alkyl substituted with (Z)_(m), C₃-C₆cycloalkyl, phenyl or phenyl substituted with (Z)_(m); R³³ is C₁-C₆alkyl, (C₁-C₆)alkyl optionally substituted with R³⁸, C₃-C₈ cycloalkyl,(C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 to E-6, E-8, E-14to E-21, C₂-C₆ alkenyl, (C₂-C₆)alkenyl optionally substituted with R³⁸,C₃-C₆ alkynyl, (C₃-C₆)alkynyl optionally substituted with R³⁸, phenyl,phenyl substituted with (Z)_(m), D-1, D-2, D-4 to D-6, D-8 to D-10, D-12to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38; R³⁴ is a hydrogen atom,C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substituted with R³⁸, C₃-C₈cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 toE-6, E-8, E-14 to E-21, C₂-C₆ alkenyl, (C₂-C₆)alkenyl optionallysubstituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₆) alkynyl optionallysubstituted with R³⁸, phenyl, phenyl substituted with (Z)_(m), D-1 toD25 or D-27 to D-38, or optionally forms a ring together with R³⁵; R³⁵is a hydrogen atom, C₁-C₆ alkyl, (C₁-C₆)alkyl optionally substitutedwith R³⁸, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(m), or R³⁵optionally forms, together with R³⁴, a C₂-C₅ alkylene chain to form a 3-to 6-membered ring together with the nitrogen atom attached to R³⁴ andR³⁵, wherein the alkylene chain optionally comprises an oxygen atom,sulfur atom or nitrogen atom, and may optionally be substituted with ahalogen atom, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, a —CHO group, aC₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonyl group, a phenyl group,a phenyl group substituted with (Z)_(m) or an oxo group; R³⁶ is ahydrogen atom, C₁-C₈ alkyl, (C₁-C₈)alkyl optionally substituted withR³⁸, C₃-C₈ cycloalkyl, (C₃-C₈)cycloalkyl optionally substituted withR³⁸, E-2 to E-6, E-8, E-14 to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyloptionally substituted with R³⁸, C₃-C₈ alkynyl, (C₃-C₈) alkynyloptionally substituted with R³⁸, —C(O)R³⁹, —C(O)C(O)R⁴⁰, —C(O)OR⁴⁰,—C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(S)R³⁹, —C(S)OR⁴⁰,—C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹, —S(O)₂R⁴⁰, —S(O)₂N(R⁴²)R⁴¹,—Si(R^(14a))(R^(14b))R¹⁴, (P(O)(OR⁴³)₂ or —P(S)(OR⁴³)₂; R³⁷ is C₁-C₈alkyl, (C₁-C₈)alkyl optionally substituted with R³⁸, C₃-C₈ cycloalkyl,(C₃-C₈)cycloalkyl optionally substituted with R³⁸, E-2 to E-6, E-8, E-14to E-21, C₃-C₈ alkenyl, (C₃-C₈)alkenyl optionally substituted with R³⁸,C₃-C₈ alkynyl, (C₃-C₈)alkynyl optionally substituted with R³⁸, —C(O)R³⁹,—C(O)C(O)R⁴⁰, —C(O)OR⁴⁰, —C(O)C(O)OR⁴⁰, —C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹,—C(S)R³⁹, —C(S)OR⁴⁰, —C(S)SR⁴⁰, —C(S)N(R⁴²)R^(4I), —SH, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, phenylthio, phenylthio substituted with (Z)_(m),—P(O)(OR⁴³)₂ or —P(S)(OR⁴³)₂; R³⁸ is a halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈ halocycloalkyl, E-5, E-6, E-9, E-10, E-12, E-14, E-15,E-18, E-19, E-21, —OH, —OR⁴⁰, —OC(O)R³⁹, —OC(O)OR⁴⁰, —OC(O)N(R⁴²)R⁴¹,—OC(S)N(R⁴²)R⁴¹, —SH, —S(O)_(n)R⁴⁰, —SC(O)R³⁹, —SC(O)OR⁴⁰,—SC(O)N(R⁴²)R⁴¹, —SC(S)N(R⁴²)R⁴¹, —N(R⁴²)R⁴¹, —N(R⁴²)C(O)R³⁹,—N(R⁴²)C(O)OR⁴⁰, —N(R⁴²)C(O)SR⁴⁰, —N(R⁴²)C(O)N(R⁴²)R⁴¹,—N(R⁴²)C(S)N(R⁴²)R⁴¹, —N(R⁴²)S(O)₂R⁴⁰, —C(O)R³⁹, —C(O)OH, —C(O)OR⁴⁰,—C(O)SR⁴⁰, —C(O)N(R⁴²)R⁴¹, —C(O)C(O)OR⁴⁰, —C(S)SR⁴⁰, —C(S)N(R⁴²)R⁴¹,—Si(R^(14a))(R^(14b))R¹⁴, —P(O)(OR⁴³)₂, —P(S)(OR⁴³)₂, —P(phenyl)₂,—P(O)(phenyl)₂, phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38;R³⁹ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl, (C₁-C₄)alkyloptionally substituted with R⁴⁴, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl,E-5, E-6, E-14, E-15, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₅-C₁₀cycloalkenyl, C₅-C₁₀ halocycloalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl,phenyl, phenyl substituted with (Z)_(m), or D-1 to D-38; R⁴⁰ is C₁-C₆alkyl, C₁-C₆ haloalkyl, (C₁-C₄)alkyl optionally substituted with R⁴⁴,C₃-C₆ cycloalkyl, E-5, E-6, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₃-C₈alkynyl or phenyl; R⁴¹ is a hydrogen atom, C₁-C₆ alkyl, C₁-C₆ haloalkyl,(C₁-C₄)alkyl optionally substituted with R⁴⁴, C₃-C₆ cycloalkyl, E-5,E-6, E-14, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₃-C₈ alkynyl, phenyl,phenyl substituted with (Z)_(m), D-1 to D-25 or D-27 to D-38, oroptionally forms a ring together with R⁴²; R⁴² is a hydrogen atom, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl or C₃-C₆alkynyl, or R⁴² optionally forms, together with R⁴¹, a C₂-C₅ alkylenechain to form a 3- to 6-membered ring together with the nitrogen atomattached to R⁴¹ and R⁴², wherein the alkylene chain optionally comprisesan oxygen atom, sulfur atom or nitrogen atom, and may optionally besubstituted with a halogen atom, a C₁-C₄ alkyl group, a C₁-C₄ alkoxygroup, a —CHO group, a C₁-C₄ alkylcarbonyl group, a C₁-C₄ alkoxycarbonylgroup, a phenyl group or a phenyl group substituted with (Z)_(m); R⁴³ isC₁-C₆ alkyl or C₁-C₆ haloalkyl; R⁴⁴ is cyano, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, E-5, E-6, E-14, E-15, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,phenoxy, phenoxy substituted with (Z)_(m), C₁-C₄ alkylthio, C₁-C₄haloalkylthio, phenylthio, phenylthio substituted with (Z)_(m), C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylsulfonyl, phenylsulfonyl, phenylsulfonylsubstituted with (Z)_(m), —N(R⁴⁶)R⁴⁵, C₁-C₄ alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylaminocarbonyl,di(C₁-C₄ alkyl)aminocarbonyl, tri(C₁-C₄ alkyl)silyl, phenyl, phenylsubstituted with (Z)_(m), or D-1 to D-38; R⁴⁵ is a hydrogen atom, C₁-C₄alkyl, C₁-C₄ alkylcarbonyl, C₁-C₄ haloalkylcarbonyl, alkoxycarbonyl,phenylcarbonyl or phenylcarbonyl substituted with (Z)_(m); R⁴⁶ is ahydrogen atom or C₁-C₄ alkyl; m is an integer of 1, 2, 3, 4 or 5; n isan integer of 0, 1, 2, 3 or 4; p is an integer of 0, 1, 2, 3, 4, 5, 6,7, 8 or 9; r is an integer of 0, 1 or 2; and t is an integer of 0 or 1.2. The oxime-substituted amide compound according to claim 1, wherein:G¹ is a structure represented by any one of G¹-1 to G¹-5, G¹-7 to G¹-13,G¹-16, G¹-19, G¹-20, G¹-23, G¹-27, G¹-30 to G¹-33, G¹-41, G¹-43 to G¹-46and G¹-49 to G¹-51; G² is a structure represented by any one of G²-1 toG²-7, G²-9 to G²-12, G²-14, G²-16 and G²-17; X¹ is a halogen atom,cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆ cycloalkyl, alkoxy,haloalkoxy, alkylthio, C₁-C₄ haloalkylthio, —NH₂, phenyl or D-3; X² is ahydrogen atom or a halogen atom, provided that when G¹ is a structurerepresented by G¹-27 and X¹ is dihalomethyl, X² is a hydrogen atom; X³is a hydrogen atom, a halogen atom, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆cycloalkyl, C₁-C₄ alkoxy, —NH₂ or phenyl; X⁴ is a hydrogen atom, ahalogen atom or trifluoromethyl; X⁵ is a hydrogen atom or a halogenatom; Y¹ is a hydrogen atom, a halogen atom, cyano, nitro, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkoxymethyl, E-9, alkoxy, C₁-C₄ haloalkoxy,phenoxy, C₁-C₄ alkylthio or)-C(R¹⁰)═NOR¹¹, or optionally forms a ringtogether with Y²; Y² is a hydrogen atom, a halogen atom, cyano, methyl,trifluoromethyl, alkoxy, C₁-C₄ haloalkoxy, phenoxy or C₁-C₄ alkyothio,or may form the after-mentioned ring together with Y³, or Y² optionallyforms, together with Y¹, —OCH₂O—, —CH₂CH₂CH₂CH₂—, —OCH₂CH₂O— or—CH═CHCH═CH— to form a 5-membered ring or a 6-membered ring togetherwith the carbon atoms attached to Y¹ and Y², wherein hydrogen atoms onthe respective ring-constituting carbon atoms are optionally besubstituted with a halogen atom or methyl; Y³ is a hydrogen atom, ahalogen atom, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxymethyl, C₃-C₆ cycloalkyl, —OR⁷, —S(O)_(r)R⁷, —N(R⁹)R⁸, —C(O)R¹⁰,—C(R¹⁰)═NOR¹¹, M-3, —C(O)NH₂, M-7, —C(S)NH₂, —SO₂N(CH₃)₂, C₂-C₄ alkenyl,C₂-C₆ alkynyl, (C₂-C₆)alkynyl substituted with R⁶, phenyl, phenylsubstituted with (Z)_(m), D-3, D-7, D-11, D-22, D-28 or D-29, oroptionally forms a ring together with Y⁴, or Y³ may form, together withY², —OCH₂O—, —OCH₂CH₂O— or —CH═CHCH═CH— to form a 5-membered ring or a6-membered ring together with the carbon atoms attached to Y² and Y³,wherein hydrogen atoms on the respective ring-constituting carbon atomsare optionally substituted with a halogen atom or methyl; Y⁴ is ahydrogen atom, a halogen atom, cyano, methyl, trifluoromethyl ormethoxy, or Y⁴ optionally forms, together with Y³, —OCH₂O—, —OCH₂CH₂O—or —CH═CHCH═CH— to form a 5-membered ring or a 6-membered ring togetherwith the carbon atoms attached to Y³ and Y⁴, wherein hydrogen atoms onthe respective ring-constituting carbon atoms are optionally substitutedwith a halogen atom or methyl; Y⁵ is a hydrogen atom, a halogen atom ormethyl; Z is a halogen atom, cyano, nitro, C₁-C₄ alkyl, trifluoromethyl,methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl,methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl,trifluoromethylsulfonyl or phenyl, such that when m or n is an integerof at least 2, the respective Z's may be identical with or differentfrom one another, and when there are two neighboring Z's, the twoneighboring Z's optionally form —CH═CH—CH═CH—, to form a 6-membered ringtogether with the carbon atoms attached to the two Z's; R¹ is C₁-C₆alkyl, C₁-C₄ haloalkyl, (C₁-C₄)alkyl optionally substituted with R¹⁸,C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, E-2 to E-6, E-8, E-14, E-15,E-17, C₃-C₆ alkenyl, C₃-C₄ haloalkenyl, C₃-C₆ alkynyl, C₃-C₄ haloalkynylor phenyl; R² is a hydrogen atom, C₁-C₄ alkyl, fluoromethyl,trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, cyclopropyl, cyclobutyl or phenyl, or optionallyforms a ring together with R³, provided that when G¹ is a structurerepresented by G¹-1, X¹ is a chlorine atom, X², X³ and X⁵ are hydrogenatoms, X⁴ is a hydrogen atom or a chlorine atom, G² is a structurerepresented by G²-1, Y³ is a chlorine atom, and Y¹, Y², Y⁴ and Y⁵ arehydrogen atoms, R² is C₁-C₄ alkyl, fluoromethyl, trifluoromethyl,methoxymethyl, methylthiomethyl, methylsulfinylmethyl,methylsulfonylmethyl, cyclopropyl, cyclobutyl or phenyl; R³ is ahydrogen atom or C₁-C₄ alkyl, or R³ optionally forms, together with R²,a C₂-C₅ alkylene chain to form a 3- to 6-membered ring together with thecarbon atom attached to R² and R³, wherein the alkylene chain optionallycomprises an oxygen atom or sulfur atom; R⁴ is a hydrogen atom, C₁-C₄alkyl, (C₁-C₂)alkyl substituted with R¹⁹, C₃-C₆ cycloalkyl, C₂-C₄alkenyl, C₂-C₄ alkynyl, —C(O)R²⁰, —C(O)OR²¹, C₁-C₄ alkoxy or C₁-C₄haloalkylthio; R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₃-C₆ cycloalkyl;R⁶ is a halogen atom, C₃-C₆ cycloalkyl, hydroxy(C₃-C₆)cycloalkyl, C₃-C₄alkenyl, C₅-C₆ cycloalkenyl, —OH, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,—Si(R^(14a))(R^(14b))R¹⁴, phenyl, phenyl substituted with (Z)_(m), D-1,D-2, D-4, D-12 or D-32; R⁷ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄haloalkenyl, C₃-C₄ haloalkynyl, phenyl or phenyl substituted with(Z)_(m); R⁸ and R⁹ together form a C₄-C₅ alkylene chain to form a 5- to6-membered ring together with the nitrogen atom attached to R⁸ and R⁹,and the alkylene chain optionally comprises an oxygen atom or sulfuratom; R¹⁰ is a hydrogen atom, C₁-C₄ alkyl or cyclopropyl; R¹¹ is C₁-C₄alkyl or C₁-C₄ haloalkyl; R¹⁴ is C₁-C₄ alkyl or phenyl; each of R^(14a)and R^(14b) is independently C₁-C₄ alkyl; R¹⁶ is —C(O)R¹⁰ or —C(O)OR¹¹;R¹⁷ is C₁-C₄ alkyl, and when p is 2, the respective R¹⁷'s are identicalwith or different from one another; R¹⁸ is a halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆ halocycloalkyl, E-2 to E-6, E-8, E-9, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, —C(R³²)═NOR³³, M-3, M-4, C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄ haloalkylaminocarbonyl, —C(S)NH₂,trimethylsilyl, phenyl, phenyl substituted with (Z)_(m), D-1, D-2, D-4to D-6, D-8 to D-10, D-12, D-14, D-15, D-17 or D-32; R¹⁹ is cyano,—OR³⁶, —C(O)NH₂ or —C(S)NH₂; R²⁰ is a hydrogen atom, C₁-C₄ alkyl, C₁-C₄alkoxymethyl, C₁-C₄ alkylthiomethyl, C₁-C₄ alkylsulfonylmethyl, C₃-C₄cycloalkyl or C₂-C₄ alkenyl; R²¹ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy(C₁-C₂)alkyl, allyl or propargyl; R³² is a hydrogen atom, C₁-C₄alkyl or C₃-C₆ cycloalkyl; R³³ is C₁-C₄ alkyl or C₁-C₄ haloalkyl; R³⁶ isC₁-C₄ alkyl, C₂-C₄ haloalkyl, C₁-C₄ alkylcarbonyl, C₃-C₆cycloalkylcarbonyl or C₁-C₄ alkoxycarbonyl; m is an integer of 1, 2 or3; n is an integer of 0, 1 or 2; and p is an integer of 0, 1 or
 2. 3.The oxime-substituted amide compound according to claim 2, wherein: G¹is a structure represented by any one of G¹-1 to G¹-4, G¹-7 to G¹-9,G¹-11 to G¹-13, G¹-16, G¹-20, G¹-27, G¹-30, G¹-32, G¹-33, G¹-44 andG¹-50; G² is a structure represented by any one of G 2-1 to G²-3, G²-6,G²-9 to G²-12 and G²-17; X¹ is a halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthioor phenyl; X³ is a hydrogen atom, methyl, trifluoromethyl or phenyl; Y¹is a hydrogen atom, a halogen atom, methyl, trifluoromethyl, E-9,methoxy or —C(R¹⁰)═NOR¹¹, or optionally forms a ring together with Y²;Y² is a hydrogen atom, a halogen atom, cyano or C₁-C₄ alkoxy, oroptionally forms a ring together with Y³, or Y² optionally forms,together with Y¹, —CH═CHCH═CH— to form a 6-membered ring together withthe carbon atoms attached to Y¹ and Y²; Y³ is a hydrogen atom, a halogenatom, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxymethyl, —OR⁷,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, —C(O)R¹⁰,—C(R¹⁰)═NOR¹¹, M-7, C₂-C₄ alkenyl, C₂-C₆ alkynyl, (C₂-C₆)alkynylsubstituted with R⁶, phenyl, phenyl substituted with (Z)_(m), D-3, D-7or D-22, or Y³ optionally forms, together with Y², —CH═CHCH═CH— to forma 6-membered ring together with the carbon atoms attached to Y² and Y³;Y⁴ is a hydrogen atom, a halogen atom, trifluoromethyl or methoxy; Y⁵ isa hydrogen atom or a halogen atom; Z is a halogen atom, cyano, nitro,C₁-C₄ alkyl, trifluoromethyl, methoxy, trifluoromethoxy,trifluoromethylthio or phenyl, when m or n is an integer of at least 2,the respective Z's are identical with or different from one another, andwhen there are two neighboring Z's, the two neighboring Z's optionallyform —CH═CH—CH═CH— to form a 6-membered ring together with the carbonatoms attached to the two Z's; R¹ is C₁-C₆ alkyl, C₁-C₄ haloalkyl,(C₁-C₄)alkyl substituted with R¹⁸, C₃-C₆ cycloalkyl, E-2, E-14, C₃-C₆alkenyl, C₃-C₄ haloalkenyl, C₃-C₆ alkynyl or phenyl; R² is a hydrogenatom, C₁-C₄ alkyl or phenyl, or optionally forms a ring together withR³, provided that when G¹ is a structure represented by G¹-1, X¹ is achlorine atom, X², X³ and X⁵ are hydrogen atoms, X⁴ is a hydrogen atomor a chlorine atom, G² is a structure represented by G²-1, Y³ is achlorine atom, and Y′, Y², Y⁴ and Y⁵ are hydrogen atoms, R² is C₁-C₄alkyl or phenyl; R³ is a hydrogen atom or methyl, or R³ optionallyforms, together with R², a C₂-C₅ alkylene chain to form a 3- to6-membered ring together with the carbon atom attached to R² and R³; R⁴is a hydrogen atom, C₁-C₄ alkyl, (C₁-C₂)alkyl substituted with R¹⁹,cyclopropyl, allyl, propargyl, C₁-C₄ alkylcarbonyl, C₁-C₄ alkoxycarbonylor C₁-C₄ haloalkylthio; R⁵ is C₁-C₄ alkyl; R⁶ is a halogen atom, C₃-C₆cycloalkyl, hydroxy(C₃-C₆)cycloalkyl, C₅-C₆ cycloalkenyl, —OH, tri(C₁-C₄alkyl)silyl, phenyl, phenyl substituted with (Z)_(m) or D-32; R⁷ isC₁-C₄ alkyl, C₁-C₄ haloalkyl, phenyl or phenyl substituted with (Z)_(m);R¹⁰ is a hydrogen atom or C₁-C₄ alkyl; R¹¹ is C₁-C₄ alkyl; R¹⁷ ismethyl; R¹⁸ is cyano, C₃-C₆ cycloalkyl, E-5, E-9, C₁-C₄ alkoxy, C₁-C₄alkylthio, —C(R³²)═NOR³³, M-4, C₁-C₄ alkoxycarbonyl, C₁-C₄haloalkylaminocarbonyl, trimethylsilyl, phenyl, phenyl substituted with(Z)_(m), D-1, D-5, D-10 or D-32; R¹⁹ is C₁-C₄ alkoxy; R³² is a hydrogenatom or C₁-C₄ alkyl; R³³ is C₁-C₄ alkyl; and r is
 0. 4. Theoxime-substituted amide compound according to claim 3, wherein: G¹ is astructure represented by any one of G¹-1 to G¹-3, G¹-7, G¹-9, G¹-11,G¹-12, G¹-16, G¹-27, G¹-32, G¹-33 and G¹-50; G² is a structurerepresented by any one of G²-1, G²-2, G²-6, G²-9 and G²-10; W is anoxygen atom; X¹ is a halogen atom, nitro, methyl, difluoromethyl ortrifluoromethyl; X² is a hydrogen atom, and when G¹ is a structurerepresented by G¹-27 and X¹ is trifluoromethyl, X² may be a halogenatom; X³ is a hydrogen atom or methyl; X⁴ is a hydrogen atom or ahalogen atom; X⁵ is a hydrogen atom; Y¹ is a hydrogen atom, a halogenatom, methyl, trifluoromethyl or methoxy; Y² is a hydrogen atom, ahalogen atom or cyano, or optionally forms a ring together with Y³; Y³is a hydrogen atom, a halogen atom, cyano, methyl, trifluoromethyl,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₄ alkenyl, C₂-C₆alkynyl, (C₂-C₆)alkynyl substituted with R⁶, phenyl, D-3 or D-7; or Y³optionally forms, together with Y², —CH═CHCH═CH— to form a 6-memberedring together with carbon atoms attached to Y² and Y³; Y⁴ is a hydrogenatom or a halogen atom; R¹ is C₁-C₆ alkyl, C₁-C₄ haloalkyl, (C₁-C₄)alkylsubstituted with R¹⁸, C₃-C₆ cycloalkyl, C₃-C₆ alkenyl, C₃-C₄haloalkenyl, C₃-C₆ alkynyl or phenyl; R² is a hydrogen atom, methyl orethyl, or optionally forms a cyclopropyl ring together with R³, providedthat when G¹ is a structure represented by G¹-1, X¹ is a chlorine atom,X², X³ and X⁵ are hydrogen atoms, X⁴ is a hydrogen atom or a chlorineatom, G² is a structure represented by G²-1, Y³ is a chlorine atom, andY¹, Y², Y⁴ and Y⁵ are hydrogen atoms, R² is methyl or ethyl; R³ is ahydrogen atom or methyl, or R³ optionally forms a cyclopropyl ringtogether with R²; R⁴ is a hydrogen atom, C₁-C₄ alkylcarbonyl, C₁-C₄alkoxycarbonyl or C₁-C₄ haloalkylthio; R⁵ is methyl; R⁶ is a halogenatom, C₃-C₆ cycloalkyl, —OH, trimethylsilyl or phenyl; R¹⁰ is methyl;R¹¹ is methyl or ethyl; R¹⁸ is cyano, C₃-C₆ cycloalkyl, E-5, C₁-C₄alkoxy, C₁-C₄ alkylthio, —C(R³²)═NOR³³, trimethylsilyl, phenyl, phenylsubstituted with (Z)_(m), D-5, D-10 or D-32; R³² is methyl; R³³ ismethyl or ethyl; and P is
 0. 5. The oxime-substituted amide compoundaccording to claim 4, wherein: G¹ is a structure represented by any oneof G¹-1 to G¹-3, G¹-7, G¹-11, G¹-12, G¹-16, G¹-27 and G¹-33; G² is astructure represented by G²-1 or G²-2; X¹ is a halogen atom, methyl,difluoromethyl or trifluoromethyl; X² is a hydrogen atom; X⁴ is ahydrogen atom; Y¹ is a halogen atom; Y² is a hydrogen atom or a halogenatom; Y³ is a halogen atom, cyano, methyl, trifluoromethyl, C₁-C₄haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₆ alkynyl, cyclopropylethynyl,trimethylsilylethynyl or phenylethynyl; Y⁵ is a hydrogen atom; R¹ isC₁-C₆ alkyl, C₁-C₄ haloalkyl, (C₁-C₄)alkyl substituted with R¹⁸, C₃-C₆cycloalkyl, C₃-C₆ alkenyl, C₃-C₄ haloalkenyl or C₃-C₆ alkynyl; R² is ahydrogen atom or methyl, provided that when G² is a structurerepresented by G²-1, R² is methy; R³ is a hydrogen atom; R⁴ is ahydrogen atom; R¹⁸ is C₃-C₆ cycloalkyl, trimethylsilyl, phenyl, phenylsubstituted with (Z)_(m) or D-32; Z a halogen atom, cyano, nitro,methyl, trifluoromethyl or trifluoromethoxy, and when m is an integer ofat least 2, respective Z's are identical with or different from oneanother; and n is
 1. 6. The oxime-substituted amide compound accordingto claim 1, wherein: G¹ is a structure represented by G¹-1; X¹ is ahalogen atom, methyl, difluoromethyl or trifluoromethyl; and X², X³, X⁴and X⁵ are hydrogen atoms.
 7. The oxime-substituted amide compoundaccording to claim 1, wherein: G¹ is a structure represented by G¹-2 orG¹-3; X¹ is a halogen atom, methyl or trifluoromethyl; and X², X³, X⁴and X⁵ are hydrogen atoms.
 8. The oxime-substituted amide compoundaccording to claim 1, wherein: G¹ is a structure represented by G¹-7; X¹is trifluoromethyl; and X³ and X⁴ are hydrogen atoms.
 9. Theoxime-substituted amide compound according to claim 1, wherein: G¹ is astructure represented by G¹-11 or G¹-12; X¹ is a halogen atom, methyl ortrifluoromethyl; and X², X³ and X⁴ are hydrogen atoms.
 10. Theoxime-substituted amide compound according to claim 1, wherein: G¹ is astructure represented by G¹-16; X¹ is trifluoromethyl; X² and X⁴ arehydrogen atoms; and R⁵ is methyl.
 11. The oxime-substituted amidecompound according to claim 1, wherein: G¹ is a structure represented byG¹-27; X¹ is difluoromethyl or trifluoromethyl; X² is a hydrogen atom;and R⁵ is methyl.
 12. The oxime-substituted amide compound according toclaim 1, wherein: G¹ is a structure represented by G¹-33; X¹ isdifluoromethyl or trifluoromethyl; and X³ is methyl.
 13. Theoxime-substituted amide compound according to claim 1, wherein: G² is astructure represented by G²-2; Y¹ is a halogen atom; Y² is a hydrogenatom or a halogen atom; Y³ is a halogen atom, cyano, methyl,trifluoromethyl, C₁-C₄ haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₆ alkynyl,cyclopropylethynyl, trimethylsilylethynyl or phenylethynyl; Y⁴ is ahydrogen atom or a halogen atom; R¹⁰ is methyl; and R¹¹ is methyl orethyl.
 14. An intermediate of the oxime-substituted amide compound of inclaim 1, which is represented by formula (IIa):

wherein: Y¹ is a halogen atom; Y² is a hydrogen atom, a halogen atom orcyano; Y³ is a halogen atom, cyano, methyl, trifluoromethyl, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₄ alkenyl, C₂-C₆ alkynyl,(C₂-C₆)alkynyl substituted with R⁶, D-3 or D-7; Y⁴ is a hydrogen atom ora halogen atom; R¹ is C₁-C₆ alkyl, C₁-C₄ haloalkyl, (C₁-C₄)alkylsubstituted with R¹⁸, C₃-C₆ cycloalkyl, C₃-C₆ alkenyl, C₃-C₄haloalkenyl, C₃-C₆ alkynyl or phenyl; R² is a hydrogen atom, methyl orethyl; R³ is a hydrogen atom or methyl, or R³ optionally forms acyclopropyl ring together with R²; R⁶ is a halogen atom, C₃-C₆cycloalkyl, —OH, trimethylsilyl or phenyl; R¹⁰ is methyl; R¹¹ is methylor ethyl; R¹⁸ is cyano, C₃-C₆ cycloalkyl, E-5, C₁-C₄ alkoxy, C₁-C₄alkylthio, —C(R³²)═NOR³³, trimethylsilyl, phenyl, phenyl substitutedwith (Z)_(m), D-5, D-10 or D-32; R³² is methyl; R³³ is methyl or ethyl;Z is a halogen atom, cyano, nitro, C₁-C₄ alkyl, trifluoromethyl,methoxy, trifluoromethoxy, trifluoromethylthio or phenyl, when m or n isan integer of at least 2, the respective Z's are identical with ordifferent from one another, and when there are two neighboring Z's, thetwo neighboring Z's optionally form —CH═CH—CH═CH— to form a 6-memberedring together with carbon atoms attached to the two Z's; m is 1, 2 or 3;n is an integer of 0, 1 or 2; and p is O.
 15. An intermediate of theoxime-substituted amide compound of claim 1, which is represented byformula (IVa):

wherein: G¹ is a structure represented by any one of G¹-1, G¹-2 andG¹-3:

X¹ is a halogen atom, nitro, methyl, difluoromethyl or trifluoromethyl;X², X³ and X⁵ are hydrogen atoms; X⁴ is a hydrogen atom, and when G¹ isG¹-1, X⁴ is optionally a halogen atom; Y¹ is a halogen atom; Y² is ahydrogen atom, a halogen atom or cyano; Y³ is a halogen atom, cyano,methyl, trifluoromethyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,)-C(R¹⁰)═NOR¹¹,C₂-C₄ alkenyl, C₂-C₆ alkynyl, (C₂-C₆)alkynyl substituted with R⁶, D-3 orD-7; Y⁴ is a hydrogen atom or a halogen atom; R² is a hydrogen atom ormethyl; R⁶ is a halogen atom, C₃-C₆ cycloalkyl, —OH, trimethylsilyl orphenyl; R¹⁰ is methyl; R¹¹ is methyl or ethyl; and n is
 0. 16. Anintermediate of the oxime-substituted amide compound of claim 1, whichis represented by formula (VIa) or (VIIIa):

wherein: A is C—H or N; G¹ is a structure represented by any one of G¹-1to G¹-3, G¹-7, G¹-9, G¹-11, G¹-12, G¹-16, G¹-27, G¹-32, G¹-33 and G¹-50:

X¹ is a halogen atom, nitro, methyl, difluoromethyl or trifluoromethyl;X² is a hydrogen atom, and when G¹ is a structure represented by G¹-27and X¹ is trifluoromethyl, X² is optionally a halogen atom; X³ is ahydrogen atom or methyl; X⁴ is a hydrogen atom or a halogen atom; X⁵ isa hydrogen atom; Y¹ is a halogen atom; Y² is a hydrogen atom, a halogenatom or cyano; Y³ is a halogen atom, cyano, methyl, trifluoromethyl,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, —C(R¹⁰)═NOR¹¹, C₂-C₄ alkenyl, C₂-C₆alkynyl, (C₂-C₆)alkynyl substituted with R⁶, D-3 or D-7; Y⁴ is ahydrogen atom or a halogen atom; R² is a hydrogen atom, methyl or ethyl,provided that when G¹ is a structure represented by G¹-1, X¹ is achlorine atom, X², X³ and X⁵ are hydrogen atoms, X⁴ is a hydrogen atomor a chlorine atom, A is C—H, Y³ is a chlorine atom, and Y¹, Y² and Y⁴are hydrogen atoms, R² is methyl or ethyl; R³ is a hydrogen atom ormethyl, or R³ optionally forms a cyclopropyl ring together with R²; R⁵is methyl; R⁶ is a halogen atom, C₃-C₆ cycloalkyl, —OH, trimethylsilylor phenyl; R¹⁰ is methyl; R¹¹ is methyl or ethyl; n is 0; and r is 0.17. A pesticidal composition, comprising the oxime-substituted amidecompound of claim 1, as an active ingredient.
 18. An agriculturalfungicidal or nematocidal composition, comprising the oxime-substitutedamide compound of claim 1, as an active ingredient.
 19. A process,comprising applying the agricultural fungicidal or nematocidalcomposition of claim 18 to a plant by foliar treatment.
 20. A process,comprising applying the agricultural fungicidal or nematocidalcomposition of claim 18 a soil in which plants grow.
 21. A process,comprising applying the agricultural fungicidal or nematocidalcomposition of claim 18 to at least one selected from the groupconsisting of a seed, a tuberous root, and a rhizome of a plant.
 22. Anantifungal or parasitical composition for a mammal or bird, thecomposition comprising the oxime-substituted amide compound of claim 1,as an active ingredient.
 23. The composition according to claim 22,which is adapted to treat a mammal or a bird against internal parasitesby oral administration.
 24. The composition according to claim 22, whichis adapted to treat a mammal or a bird against internal parasites byparenteral administration.
 25. The composition according to claim 22,which is adapted to treat a mammal or a bird against internal parasitesby percutaneous administration.